Ammonia → HCID 178517908, compound

HRID 2200255Notes

Reaction equation

HRID 2200255 reaction equation
S[C:2]1[N:3]=[C:4]([OH:11])[C:5]2[CH2:10][CH2:9][CH2:8][C:6]=2[N:7]=1.N>O.[Ni]>[N:7]1[C:6]2[CH2:8][CH2:9][CH2:10][C:5]=2[C:4]([OH:11])=[N:3][CH:2]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 178518551HCID 178518551, compound

Product 1

HCID 178517908HCID 178517908, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent

Procedure

To a solution of 2-mercapto-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-ol (12.2 g, 72.5 mmol) in water (200 ml) was added Raney Ni (8 g, slurry in water) and followed by concentrated ammonia solution (27 mmol). The mixture was refluxed for 6 hour. The catalyst was filtered off. The solvent was removed under vacuum to afford 6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-ol (9.87 g, 99%). 1H NMR (CD3OD, 400 MHz) δ 8.07 (s, 1H), 2.89-2.85 (m, 2H), 2.80-2.76 (m, 2H), 2.23 (m, 1H), 2.13-2.05 (m, 2H), 1.64 (m, 1H).

Workup

  1. temperatureThe mixture was refluxed for 6 hour
  2. filtrationThe catalyst was filtered off
  3. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-41c2ead2dcd0456c9581251bcabf0b58
Source dataset
uspto-grants-2016_06
Patent number
US09359340B2

Reaction notes

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