Water → HCID 46198823, compound

HRID 1930599Notes

Reaction equation

HRID 1930599 reaction equation
[F:1][C:2]1[CH:33]=[CH:32][C:5]([CH2:6][C:7]2[C:8]3[CH2:31][S:30][CH2:29][CH2:28][C:9]=3[N:10]=[C:11]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([N:20]4[CH:24]=[C:23]([CH3:25])[N:22]=[CH:21]4)=[C:16]([O:26][CH3:27])[CH:15]=3)[N:12]=2)=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:42])C=1.C([O-])(O)=O.[Na+].O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[C:8]3[CH2:31][S:30](=[O:42])[CH2:29][CH2:28][C:9]=3[N:10]=[C:11]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([N:20]4[CH:24]=[C:23]([CH3:25])[N:22]=[CH:21]4)=[C:16]([O:26][CH3:27])[CH:15]=3)[N:12]=2)=[CH:32][CH:33]=1

Participants

6

Reactant 4

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 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

Product 1

HCID 46198823HCID 46198823, compoundYield 18.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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 (254 mg, 0.55 mmol) and meta-chloroperbenzoic acid (95 mg, 0.55 mmol) was slurrified in DCM (4 mL). Saturated NaHCO3 and water were added to the reaction mixture, the organic phase was separated and the solvent was evaporated. The crude product was purified on preparative HPLC yielding 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 6-oxide (49.0 mg, 18%).

Workup

  1. customthe organic phase was separated
  2. customthe solvent was evaporated
  3. customThe crude product was purified on preparative HPLC

Sources & evidence

ORD record
ord-3787774c5e9f4a0a9823204514aa9be1
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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