Water → HCID 11738067, compound

HRID 254165Notes

Reaction equation

HRID 254165 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]([NH:10][CH2:11][C:12]2[NH:13][CH:14]=[CH:15][N:16]=2)=[O:9])[CH:5]=[C:4]([C:17]2[O:18][CH:19]=[CH:20][CH:21]=2)[N:3]=1.[H-].[Na+].[CH3:24]I.O>CN(C=O)C>[NH2:1][C:2]1[N:7]=[C:6]([C:8]([NH:10][CH2:11][C:12]2[N:13]([CH3:24])[CH:14]=[CH:15][N:16]=2)=[O:9])[CH:5]=[C:4]([C:17]2[O:18][CH:19]=[CH:20][CH:21]=2)[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 11482987HCID 11482987, compound

Product 1

HCID 11738067HCID 11738067, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-amino-6-(2-furyl)-N-(1H-imidazol-2-ylmethyl)pyrimidine-4-carboxamide (300 mg, 1.06 mmol) in DMF (15 mL) at room temperature was treated with NaH (44 mg, 1.11 mmol), stirred for 20 min, treated with MeI (99 μl, 1.58 mmol) and stirred at room temperature for 16 h. The mixture was poured into water (30 mL), extracted with EtOAc (3×10 mL) and the combined organic phase was dried (MgSO4), concentrated in vacuo and purified by chromatography [SiO2; EtOAc] to give the title compound (180 mg, 57%) as a yellow solid.

Workup

  1. stirringstirred at room temperature for 16 h
  2. extractionextracted with EtOAc (3×10 mL)
  3. dry with materialthe combined organic phase was dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. custompurified by chromatography [SiO2; EtOAc]

Sources & evidence

ORD record
ord-cf1eab4c750e464e9a6addf413256b0c
Source dataset
uspto-grants-2011_01
Patent number
US07875600B2

Reaction notes

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