Ammonia → 6-(1-Methyl-4-phenyl-1H-imidazol-5-yl)furo[3,2-d]pyrimidin-4-amine

HRID 32593Notes

Reaction equation

HRID 32593 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[O:15][C:14]3[C:13](SC)=[N:12][CH:11]=[N:10][C:9]=3[CH:8]=2)=[C:5]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:4]=[CH:3]1.O.[NH3:25]>[Cl-].[NH4+].O1CCOCC1>[CH3:1][N:2]1[C:6]([C:7]2[O:15][C:14]3[C:13]([NH2:25])=[N:12][CH:11]=[N:10][C:9]=3[CH:8]=2)=[C:5]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:4]=[CH:3]1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 962WaterHCID 691949266-(1-methyl-4-phenyl-1H-imidazol-5-yl)-4-(methylthio)furo[3,2-d]pyrimidine2×

Product 1

HCID 691973106-(1-Methyl-4-phenyl-1H-imidazol-5-yl)furo[3,2-d]pyrimidin-4-amineYield 84%

Reagents, catalysts & solvents 2

HCID 25517Ammonium ChlorideCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of 6-(1-methyl-4-phenyl-1H-imidazol-5-yl)-4-(methylthio)furo[3,2-d]pyrimidine (Intermediate 87) (50 mg) and saturated aqueous ammonium chloride solution (2 drops) in concentrated aqueous NH3 (1 mL) and 1,4-dioxane (2 mL) was heated under microwave conditions (CEM explorer, 170° C., 150 minutes). Water (10 mL) was added, and the mixture extracted into EtOAc (2×20 mL). The combined organic phases were dried and concentrated in vacuo. Purification by flash chromatography on silica (0-5% MeOH in EtOAc) afforded the title compound as an off-white solid (38 mg, 84%);

Workup

  1. extractionthe mixture extracted into EtOAc (2×20 mL)
  2. customThe combined organic phases were dried
  3. concentrationconcentrated in vacuo
  4. customPurification by flash chromatography on silica (0-5% MeOH in EtOAc)

Sources & evidence

ORD record
ord-c07d759cb37a4acb96c19610ab838952
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Reaction notes

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