Ammonium Hydroxide → 7-(3,5-difluorophenyl)-6,7-dihydro-1H-cyclopenta[d]pyrimidine-2,4(3H,5H)-dione

HRID 2370170Notes

Reaction equation

HRID 2370170 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:17]3[O:16][C:15](=O)[NH:14][C:13](=[O:19])[C:12]=3[CH2:11][CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1.[OH-].[NH4+:21]>>[F:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:17]3[NH:21][C:15](=[O:16])[NH:14][C:13](=[O:19])[C:12]=3[CH2:11][CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 580755557-(3,5-difluorophenyl)-6,7-dihydrocyclopenta[e][1,3]oxazine-2,4(3H,5H)-dione

Product 1

HCID 580756207-(3,5-difluorophenyl)-6,7-dihydro-1H-cyclopenta[d]pyrimidine-2,4(3H,5H)-dioneYield 106.1%

Procedure

A solution of 7-(3,5-difluorophenyl)-6,7-dihydrocyclopenta[e][1,3]oxazine-2,4(3H,5H)-dione (700 mg, 2.64 mmol) in concentrated ammonium hydroxide (50 mL, 1284 mmol) was heated at 100° C. in a high-pressure (350 mL) vessel overnight. The reaction mixture was cooled and concentrated in vacuum to give crude 7-(3,5-difluorophenyl)-6,7-dihydro-1H-cyclopenta[d]pyrimidine-2,4(3H,5H)-dione (740 mg, 2.80 mmol, 106% yield). LC-MS (M+H)+=265.0.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-47dfab12585244368f93e80ff7712be5
Source dataset
uspto-grants-2014_04
Patent number
US08710061B2

Reaction notes

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