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

HRID 32583Notes

Reaction equation

HRID 32583 reaction equation
[CH:1]1([N:4]2[C:8]([C:9]3[S:19][C:12]4[N:13]=[CH:14][N:15]=[C:16](SC)[C:11]=4[CH:10]=3)=[C:7]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:6]=[CH:5]2)[CH2:3][CH2:2]1.[NH3:26].[NH4+].[Cl-]>O1CCOCC1.C(Cl)Cl.O>[CH:1]1([N:4]2[C:8]([C:9]3[S:19][C:12]4[N:13]=[CH:14][N:15]=[C:16]([NH2:26])[C:11]=4[CH:10]=3)=[C:7]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:6]=[CH:5]2)[CH2:3][CH2:2]1

Participants

7

Reactant 3

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 691961746-(1-cyclopropyl-4-phenyl-1H-imidazol-5-yl)-4-(methylthio)thieno[2,3-d]pyrimidine2×

Product 1

HCID 103369216-(1-Cyclopropyl-4-phenyl-1H-imidazol-5-yl)thieno[2,3-d]pyrimidin-4-amineYield 35%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

6-(1-cyclopropyl-4-phenyl-1H-imidazol-5-yl)-4-(methylthio)thieno[2,3-d]pyrimidine (Intermediate 71) (25 mg), NH3 (aq. conc) and NH4Cl (sat. aq.) in dioxane (2 mL) were heated under microwave conditions (CEM explorer, 170° C., 4 hours). The reaction mixture was diluted with DCM and water. The aqueous layer was extracted with DCM and then the combined organics were concentrated. The crude product was purified by flash chromatography on silica eluting with Hex:EtOAc (1:1 to 100% EtOAc, then MeOH:EtOAc 95:5) to afford the title compound as a solid (8 mg, 35%);

Workup

  1. extractionThe aqueous layer was extracted with DCM
  2. concentrationthe combined organics were concentrated
  3. customThe crude product was purified by flash chromatography on silica eluting with Hex

Sources & evidence

ORD record
ord-afcdcf03b5b94425a0b4d98be9dea0a6
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Reaction notes

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