ChemicalBook CAS DataBase List 4-chloro-6-iodo-7H-pyrrolo[2,3-d]pyrimidine

4-chloro-6-iodo-7H-pyrrolo[2,3-d]pyrimidine synthesis

5synthesis methods

Product Name:4-chloro-6-iodo-7H-pyrrolo[2,3-d]pyrimidine
CAS Number:876343-10-1
Molecular formula:C6H3ClIN3
Molecular Weight:279.47

4-CHLORO-7-(PHENYLSULFONYL)-7H-PYRROLO[2,3-D]PYRIMIDINE

186519-89-1

876343-10-1

The general procedure for the synthesis of 4-chloro-6-iodo-7H-pyrrolo[2,3-d]pyrimidines from 4-chloro-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidines was carried out as follows: according to the literature [20], 4-chloro-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidines (1) (5.42 g, 18.5 mmol) were subjected to iodination reaction. Upon completion of the reaction, a 9:1 mixture of 2:3 (6.0 g) was obtained. The mixture was mixed with THF (125 mL) and a methanolic solution of 5 M NaOH (21 mL). After stirring for 2 hours at room temperature, saturated aqueous NH4Cl solution (125 mL) was added and the mixture was concentrated. The precipitate formed was collected by filtration and washed with water. Subsequently, the precipitate was ground with boiling acetonitrile (1 g/10 mL) to give 4-chloro-6-iodo-7H-pyrrolo[2,3-d]pyrimidine (3.96 g, 14.2 mmol, 77% yield) as a white solid with a melting point of 219 °C (decomposition) (220 °C reported in literature [20]).1H NMR (400 MHz, DMSO-d6) δ: 12.57 (s, 1H), 8.51 (s, 1H), 6.88 (s, 1H). The obtained 1H NMR data were in agreement with those reported in the literature [20].

4-Chloro-6-iodo-7-phenylsulfonyl-7H-pyrrolo[2,3-d]pyrimidine

876343-09-8
82 suppliers
$75.00/100mg

876343-10-1
132 suppliers
$21.00/100mg

Yield:876343-10-1 94%

Reaction Conditions:

with methanol;sodium hydroxide in tetrahydrofuran for 1 h;

Steps:

4-Chloro-6-iodo-7H-pyrrolo [2,3-i/] yrimidine (37)
4-Chloro-6-iodo-7H-pyrrolo [2,3-i/] yrimidine (37) Compound 53 (14.4 g, 34.2 mmol) was mixed with THF (300 ml) and a NaOH/MeOH-solution (5M, 49 ml, 244 mmol) and stirred for 1 hour before a saturated aq. NH₄C1 solution (300 ml) was added. The mixture was concentrated in vacuo to remove most of the solvent before it was filtered and washed with water (2 x 30 ml). The crude product was precipitated from boiling acetonitrile (9.2 g in 100 ml). This gave 8.99 g (32.2 mmol, 94 %) of 54 as a white solid, mp 220 °C (dec); purity: 98% (HPLC), t_R = 17.5 min; 1H NMR (400 MHz, DMSO-dg) δ: 13.14 (s, 1H), 8.53 (s, 1H), 6.89 (d, J= 1.8, 1H); ¹³C NMR (100 MHz, DMSO-dg) δ: 153.8, 150.3, 148.3, 118.6, 108.2, 84.8; IR (neat, cm^"1): 2790, 1549, 1327, 983, 752; HRMS (EI, 70 eV, m/z): 278.9053 (calcd. C₆H₃N₃³⁵C1I, 278.9050, [M]⁺).

References:

NORWEGIAN UNIVERSITY OF SCIENCE AND TECHNOLOGY (NTNU);HOFF, B?rd;KASPERSEN, Svein;BUGGE, Steffen;SUNDBY, Eirik;HAN, Jin WO2015/959, 2015, A1 Location in patent:Page/Page column 63

FullText

186519-89-1
58 suppliers
$26.00/1g

876343-10-1
132 suppliers
$21.00/100mg

References

3680-69-1 Synthesis