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

HRID 32531Notes

Reaction equation

HRID 32531 reaction equation
[NH3:1].[CH3:2][N:3]1[C:7]([C:8]2[S:16][C:15]3[C:14](SC)=[N:13][CH:12]=[N:11][C:10]=3[CH:9]=2)=[C:6]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:5]=[CH:4]1>[Cl-].[NH4+].CN1C(=O)CCC1>[CH3:2][N:3]1[C:7]([C:8]2[S:16][C:15]3[C:14]([NH2:1])=[N:13][CH:12]=[N:11][C:10]=3[CH:9]=2)=[C:6]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:5]=[CH:4]1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 99972846-(1-Methyl-4-phenyl-1H-imidazol-5-yl)-4-(methylthio)thieno[3,2-d]pyrimidine

Product 1

HCID 104029616-(1-Methyl-4-phenyl-1h-imidazol-5-yl)thieno[3,2-d]pyrimidin-4-amine

Reagents, catalysts & solvents 2

HCID 25517Ammonium ChlorideCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
205 °C

Procedure

Concentrated aqueous NH3 (0.5 mL) and saturated ammonium chloride solution (one drop) were added to a solution of 6-(1-methyl-4-phenyl-1H-imidazol-5-yl)-4-(methylthio)thieno[3,2-d]pyrimidine (example 11) (40 mg) in NMP (2 mL). The vessel was sealed and heated in a microwave (CEM explorer, 200-210° C., 110 W) for 35 minutes. Dilution with water (1.5 mL) and purification by RPHPLC eluting with MeCN:H2O (2:98 to 40:60) gave the title compound as a pale brown solid (24 mg, 67.%);

Workup

  1. customThe vessel was sealed
  2. customDilution with water (1.5 mL) and purification by RPHPLC
  3. washeluting with MeCN:H2O (2:98 to 40:60)

Sources & evidence

ORD record
ord-b35f3bef73ae4ecfacc52051eb7ce45d
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Reaction notes

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