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

HRID 474253Notes

Reaction equation

HRID 474253 reaction equation
[C:1]1([CH:7]2[C:15]3[O:14][C:13](=O)[NH:12][C:11](=[O:17])[C:10]=3[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[NH3:19]>>[C:1]1([CH:7]2[C:15]3[NH:19][C:13](=[O:14])[NH:12][C:11](=[O:17])[C:10]=3[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 962WaterHCID 105373627-phenyl-6,7-dihydrocyclopenta[e][1,3]oxazine-2,4(3H,5H)-dione

Product 1

HCID 107280407-phenyl-6,7-dihydro-1H-cyclopenta[d]pyrimidine-2,4(3H,5H)-dioneYield 100%

Procedure

A solution of 7-phenyl-6,7-dihydrocyclopenta[e][1,3]oxazine-2,4(3H,5H)-dione (3.751 g, 16.36 mmol) in concentrated ammonia in water (80 mL, 16.36 mmol) was heated in a 350 mL high-pressure flask for 5 h. The solvent was removed in vacuo to give 7-phenyl-6,7-dihydro-1H-cyclopenta[d]pyrimidine-2,4(3H,5H)-dione (3.73 g, 16.34 mmol, 100% yield) as a brown solid. LC-MS (M+H)+=229.1. 1H NMR (500 MHz, DMSO-d6) δ ppm 7.34 (2H, t, J=7.5 Hz), 7.26 (1H, t, J=7.3 Hz), 7.18 (2H, d, J=7.3 Hz), 5.39 (1H, br s), 4.14 (1H, d, J=7.3 Hz), 2.43-2.68 (2H, m), 1.80-1.88 (2H, m).

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-3e4ccc2a33b240ecb9652383ec5e37a4
Source dataset
uspto-grants-2014_01
Patent number
US08637523B2

Reaction notes

Loading…