Water → 6-(1-Methyl-4-phenyl-1H-imidazol-5-yl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 32536Notes

Reaction equation

HRID 32536 reaction equation
CC(C)([O-])C.[K+].[CH3:7][N:8]1[C:12]([C:13]#[C:14][C:15]2[C:16]([NH2:21])=[N:17][CH:18]=[N:19][CH:20]=2)=[C:11]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:10]=[CH:9]1.O.C(Cl)Cl>CN1C(=O)CCC1>[CH3:7][N:8]1[C:12]([C:13]2[NH:21][C:16]3[N:17]=[CH:18][N:19]=[CH:20][C:15]=3[CH:14]=2)=[C:11]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:10]=[CH:9]1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 179658255-[(1-methyl-4-phenyl-1H-imidazol-5-yl)ethynyl]pyrimidin-4-amine2×HCID 23665647Potassium tert-butoxide

Product 1

HCID 103336046-(1-Methyl-4-phenyl-1H-imidazol-5-yl)-7H-pyrrolo[2,3-d]pyrimidineYield 33.2%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
60 °C

Procedure

Potassium tert-butoxide (84 mg) was added to 5-[(1-methyl-4-phenyl-1H-imidazol-5-yl)ethynyl]pyrimidin-4-amine (intermediate 28) (41 mg) stirred in NMP (2 mL) and heated to 60° C. for 5 hours. After cooling to ambient temperature, water (3 mL) and then DCM (10 mL) was added. The reaction mixture was washed with water (4×10 mL), dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography on silica eluting with DCM:MeOH (20:1 to 10:1) afforded the title compound as a white solid (13.6 mg, 33%);

Workup

  1. temperatureAfter cooling to ambient temperature
  2. washThe reaction mixture was washed with water (4×10 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography on silica eluting with DCM:MeOH (20:1 to 10:1)

Sources & evidence

ORD record
ord-90706556386e444fa8cdd38b3e384f05
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Reaction notes

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