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

HRID 32528Notes

Reaction equation

HRID 32528 reaction equation
[CH3:1][NH2:2].[CH3:3][S:4][C:5]1[C:6]2[S:13][C:12]([CH:14]=O)=[CH:11][C:7]=2[N:8]=[CH:9][N:10]=1.N1[CH2:21][CH2:20][NH:19][CH2:18]C1.O>C(Cl)Cl>[CH3:1][N:2]1[C:14]([C:12]2[S:13][C:6]3[C:5]([S:4][CH3:3])=[N:10][CH:9]=[N:8][C:7]=3[CH:11]=2)=[C:20]([C:21]2[CH:12]=[CH:11][CH:7]=[CH:6][CH:5]=2)[N:19]=[CH:18]1

Participants

6

Reactant 4

HCID 962WaterHCID 4837PiperazineHCID 6329MethylamineHCID 226492824-(Methylthio)thieno[3,2-d]pyrimidine-6-carbaldehyde2×

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methylamine (2M in THF, 2.5 mL) was added to a solution of 4- (methylthio)thieno[3,2-d]pyrimidine-6-carbaldehyde (intermediate 21) (105 mg) in DCM (10 mL) containing 4 Å molecular sieves (1 g). The reaction mixture was stirred for 2.5 hours, at which point PhTosMIC (149 mg) and piperazine (90 mg) were added. The reaction was stirred for a further 72 hours then additional PhTosMIC (30 mg) was added. After stirring for a further 1.5 hours the mixture was poured into water and extracted into DCM, washed with water and brine, dried, and the solvent removed. Purification by flash chromatography on silica eluting with EtOAc:hexane (25:75 to 0:1Q0) gave the title compound as a pale solid foam (95 mg, 56%);

Workup

  1. additioncontaining 4 Å molecular sieves (1 g)
  2. additionwere added
  3. additionadditional PhTosMIC (30 mg) was added
  4. stirringAfter stirring for a further 1.5 hours the mixture
  5. extractionextracted into DCM
  6. washwashed with water and brine
  7. customdried
  8. customthe solvent removed
  9. customPurification by flash chromatography on silica eluting with EtOAc:hexane (25:75 to 0:1Q0)

Sources & evidence

ORD record
ord-94ea124982294e499f1de857ccbb9686
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Reaction notes

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