Dichloromethane → 4-(4-Fluorobenzyl)-N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-7,8-dihydro-5H-thiopyrano[4,3-d]pyrimidin-2-amine

HRID 1930600Notes

Reaction equation

HRID 1930600 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([CH:11]2[C:16](=O)[CH2:15][CH2:14][S:13][CH2:12]2)=O)=[CH:4][CH:3]=1.[CH3:18][O:19][C:20]1[CH:21]=[C:22]([NH:32][C:33]([NH2:35])=[NH:34])[CH:23]=[CH:24][C:25]=1[N:26]1[CH:30]=[C:29]([CH3:31])[N:28]=[CH:27]1.C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl>CCO.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[C:11]3[CH2:12][S:13][CH2:14][CH2:15][C:16]=3[N:35]=[C:33]([NH:32][C:22]3[CH:23]=[CH:24][C:25]([N:26]4[CH:30]=[C:29]([CH3:31])[N:28]=[CH:27]4)=[C:20]([O:19][CH3:18])[CH:21]=3)[N:34]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 593337083-(2-(4-Fluorophenyl)acetyl)dihydro-2H-thiopyran-4(3H)-oneHCID 178493227HCID 178493227, compound

Product 1

HCID 593338014-(4-Fluorobenzyl)-N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-7,8-dihydro-5H-thiopyrano[4,3-d]pyrimidin-2-amine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

3-(2-(4-Fluorophenyl)acetyl)dihydro-2H-thiopyran-4(3H)-one (200 mg, 0.79 mmol), 1-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)guanidine (194 mg, 0.79 mmol) and potassium carbonate (200 mg, 1.45 mmol) was slurrified in EtOH (5 mL) and heated to 60° C. for 16 h. DCM and water were added to the cooled reaction mixture. The organic phase was separated and dried with Mg2SO4 and then the solvent was evaporated. The crude product was used as such in next step. MS (ES+) m/z 462.2 (M+H)+

Workup

  1. customThe organic phase was separated
  2. dry with materialdried with Mg2SO4
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-a14b2dcd662e4f75bef682288de3ef7e
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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