m-Chloroperbenzoic acid → HCID 59333794, compound

HRID 1930731Notes

Reaction equation

HRID 1930731 reaction equation
[CH2:1]([C:8]1[C:9]2[CH2:30][S:29][CH2:28][CH2:27][C:10]=2[N:11]=[C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH:25]=[CH:24][N:23]=[C:22]3[CH3:26])=[CH:17][CH:16]=2)[N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:39])C=1>C(Cl)Cl>[CH2:1]([C:8]1[C:9]2[CH2:30][S:29](=[O:39])[CH2:28][CH2:27][C:10]=2[N:11]=[C:12]([NH:14][C:15]2[CH:16]=[CH:17][C:18]([N:21]3[CH:25]=[CH:24][N:23]=[C:22]3[CH3:26])=[CH:19][CH:20]=2)[N:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 59333701HCID 59333701, compound

Product 1

HCID 59333794HCID 59333794, compoundYield 13.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Benzyl-N-(4-(2-methyl-1H-imidazol-1-yl)phenyl)-7,8-dihydro-5H-thiopyrano[4,3-d]pyrimidin-2-amine (90 mg, 0.22 mmol) and mCPBA (56.3 mg, 0.33 mmol) was dissolved in DCM (4 mL). The reaction was completed after 2 h. The solvent was evaporated and the crude product was purified on preparative HPLC yielding 4-benzyl-N-[4-(2-methyl-1H-imidazol-1-yl)phenyl]-7,8-dihydro-5H-thiopyrano[4,3-d]pyrimidin-2-amine 6-oxide (13.0 mg, 13.0%). MS (ES+) m/z 430.0 (M+H)+

Workup

  1. customThe solvent was evaporated
  2. customthe crude product was purified on preparative HPLC

Sources & evidence

ORD record
ord-f09719a643a74be4a536f33a935df66f
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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