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

HRID 32582Notes

Reaction equation

HRID 32582 reaction equation
C1C=C(Cl)C=C(C(OO)=O)C=1.[CH2:12]([N:14]1[C:18]([C:19]2[S:29][C:22]3[N:23]=[CH:24][N:25]=[C:26](SC)[C:21]=3[CH:20]=2)=[C:17]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:16]=[CH:15]1)[CH3:13].[NH3:36]>C(Cl)Cl>[NH3:14].[CH2:12]([N:14]1[C:18]([C:19]2[S:29][C:22]3[N:23]=[CH:24][N:25]=[C:26]([NH2:36])[C:21]=3[CH:20]=2)=[C:17]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:16]=[CH:15]1)[CH3:13]

Participants

6

Reactant 3

HCID 222Ammonia2×HCID 70297m-Chloroperbenzoic acidHCID 691949276-(1-ethyl-4-phenyl-1H-imidazol-5-yl)-4-(methylthio)thieno[2,3-d]pyrimidine2×

Product 2

HCID 222AmmoniaHCID 691942306-(1-Ethyl-4-phenyl-1H-imidazol-5-yl)thieno[2,3-d]pyrimidin-4-amineYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

mCPBA (70-75%, 160 mg) was added to a stirred solution of 6-(1-ethyl-4-phenyl-1H-imidazol-5-yl)-4-(methylthio)thieno[2,3-d]pyrimidine (Intermediate 70) (91 mg) in DCM (8 mL) and allowed to stir at ambient temperature for 45 minutes. NH3 (0.5M in dioxane) (10 mL) was then added and the reaction was allowed to stir for 2 days with further NH3 (0.5M in dioxane) (5 mL) added after 16 hours. The reaction mixture was concentrated in vacuo and the crude product purified by flash chromatography on silica eluting with isohexane:EtOAc (1:1) then 0-10% (7M NH3 in MeOH) in EtOAc to afford the title compound as a solid (40 mg, 48%);

Workup

  1. additionadded after 16 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe crude product purified by flash chromatography on silica eluting with isohexane:EtOAc (1:1)

Sources & evidence

ORD record
ord-512d1792f63a4188a1951a38d0bdde4d
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Reaction notes

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