Water → 4-(4-fluorobenzyl)-N-[4-(2-methyl-1H-imidazol-1-yl)phenyl]-7,8-dihydro-5H-thiopyrano[4,3-d]pyrimidin-2-amine 6-oxide

HRID 1930627Notes

Reaction equation

HRID 1930627 reaction equation
[F:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][C:7]2[C:8]3[CH2:29][S:28][CH2:27][CH2:26][C:9]=3[N:10]=[C:11]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([N:20]4[CH:24]=[CH:23][N:22]=[C:21]4[CH3:25])=[CH:16][CH:15]=3)[N:12]=2)=[CH:4][CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:40])C=1.O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[C:8]3[CH2:29][S:28](=[O:40])[CH2:27][CH2:26][C:9]=3[N:10]=[C:11]([NH:13][C:14]3[CH:15]=[CH:16][C:17]([N:20]4[CH:24]=[CH:23][N:22]=[C:21]4[CH3:25])=[CH:18][CH:19]=3)[N:12]=2)=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 593337504-(4-Fluorobenzyl)-N-(4-(2-methyl-1H-imidazol-1-yl)phenyl)-7,8-dihydro-5H-thiopyrano[4,3-d]pyrimidin-2-amine

Product 1

HCID 461992744-(4-fluorobenzyl)-N-[4-(2-methyl-1H-imidazol-1-yl)phenyl]-7,8-dihydro-5H-thiopyrano[4,3-d]pyrimidin-2-amine 6-oxideYield 19.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(4-Fluorobenzyl)-N-(4-(2-methyl-1H-imidazol-1-yl)phenyl)-7,8-dihydro-5H-thiopyrano[4,3-d]pyrimidin-2-amine (103 mg, 0.24 mmol) was dissolved in DCM (3 mL). mCPBA (61.8 mg, 0.36 mmol) was added and the reaction was stirred at rt for 2 h. Water was added and the product was obtained by separating the organic phase and evaporating the solvent. The crude product was purified using preparative HPLC yielding 4-(4-fluorobenzyl)-N-[4-(2-methyl-1H-imidazol-1-yl)phenyl]-7,8-dihydro-5H-thiopyrano[4,3-d]pyrimidin-2-amine 6-oxide (21.0 mg, 18.9%). MS (ES+) m/z 448.1 (M+H)+

Workup

  1. customthe product was obtained
  2. customby separating the organic phase
  3. customevaporating the solvent
  4. customThe crude product was purified

Sources & evidence

ORD record
ord-80521ff762614205bc7f56ffc489fe27
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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