2-Thioxo-1,2,3,5,6,7-hexahydro-4h-benzo[6,7]cyclohepta[1,2-d]pyrimidin-4-one → 3,5,6,7-tetrahydro-4H-benzo[6,7]cyclohepta[1,2-d]pyrimidin-4-one

HRID 1027902Notes

Reaction equation

HRID 1027902 reaction equation
S=[C:2]1[NH:7][C:6]2[C:8]3[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=3[CH2:10][CH2:11][CH2:12][C:5]=2[C:4](=[O:17])[NH:3]1>CO.[Ni]>[N:7]1[C:6]2[C:8]3[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=3[CH2:10][CH2:11][CH2:12][C:5]=2[C:4](=[O:17])[NH:3][CH:2]=1

Participants

4

Reactant 1

HCID 158571262-Thioxo-1,2,3,5,6,7-hexahydro-4h-benzo[6,7]cyclohepta[1,2-d]pyrimidin-4-one

Product 1

HCID 1358187063,5,6,7-tetrahydro-4H-benzo[6,7]cyclohepta[1,2-d]pyrimidin-4-one

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of Example 118A (170 mg, 0.7 mmol) in methanol (15 mL) was treated with Raney nickel (slurry in H2O, 1 spatula) and refluxed for 16 hours. The mixture was filtered through diatomaceous earth and washed with methanol. The filtrate was concentrated under vacuum to provide the title compound. 1H NMR (CD3OD) δ 2.24 (t, 2H), 2.40 (t, 2H), 2.59 (t, 2H), 7.27-7.34 (m, 1H), 7.36-7.42 (m, 2H), 7.60-7.66 (m, 1H), 8.14-8.18 (m, 1H). MS (M+H)+ m/z 213

Workup

  1. temperaturerefluxed for 16 hours
  2. filtrationThe mixture was filtered through diatomaceous earth
  3. washwashed with methanol
  4. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-1d07cd99ad4a42b4af7f52173f0c846e
Source dataset
uspto-grants-2014_05
Patent number
US08735411B2

Reaction notes

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