Water → HCID 178431707, compound

HRID 2226018Notes

Reaction equation

HRID 2226018 reaction equation
[I:1][N:2]1[C:7]([OH:8])=[C:6]2[CH:9]=[C:10]([CH3:12])[N:11]=[C:5]2[N:4]=[CH:3]1.[H-].[Na+].CN(C)[CH:17]=[O:18].[C:20]([O:26]CCl)(=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22].[OH2:29]>C(O)(=O)C>[I:1][N:2]1[C:7]([OH:8])=[C:6]2[C:9]([O:26][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])=[C:10]([CH3:12])[N:11]=[C:5]2[N:4]([O:29][C:17](=[O:18])[C:6]([CH3:9])([CH3:7])[CH3:5])[CH2:3]1

Participants

7

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 87885Chloromethyl pivalateHCID 178422253HCID 178422253, compound

Product 1

HCID 178431707HCID 178431707, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Ten grams of 3-iodo-4-hydroxy-6-methylpyrrolo[2,3-d]pyrimidine are allowed to react with 2.19 g of 80% sodium hydride oil dispersion and 75 ml of dimethylformamide with the exclusion of moisture. After 30 minutes, 6.02 g of chloromethyl pivalate are added. This mixture is stirred for three hours poured into water, and neutralized with acetic acid. The solid is chromatographed on silica gel with acetone-dichloromethane to yield 3-iodo-4-hydroxy-l,5-bis-(pivaloyloxy)-6-methylpyrrolo[2,3-d]pyrimidine, m.p. 155° C. initially, followed by 3-iodo-4-hydroxy-5-pivaloyloxy-6-methylpyrrolo[2,3-d]pyrimidine, m.p. 236° C.

Workup

  1. customThe solid is chromatographed on silica gel with acetone-dichloromethane

Sources & evidence

ORD record
ord-90652b30231f4b7895a6694b2138aac4
Source dataset
uspto-grants-1994_09
Patent number
US05344932

Reaction notes

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