7-chloro-3-(4-methoxy-phenyl)-1-methyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidine-2-one → 3-(4-methoxy-phenyl)-1-methyl-7-phenylamino-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidine-2-one

HRID 1243197Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]2[N:8]([CH3:21])[C:9](=[O:20])[N:10]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[CH2:11][C:5]2=[CH:4][N:3]=1>NC1C=CC=CC=1>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([N:10]2[CH2:11][C:5]3[C:6](=[N:7][C:2]([NH:10][C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)=[N:3][CH:4]=3)[N:8]([CH3:21])[C:9]2=[O:20])=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 120 °C

Procedure

The mixture of 7-chloro-3-(4-methoxy-phenyl)-1-methyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidine-2-one (65 mg, 0.21 mmol) in aniline (1.0 mL) (Aldrich) was heated to 120° C. for 1 hour. After cooling, the reaction mixture was washed with hexanes (100 mL×4) and the crude product was re-crystallized from ethyl acetate-hexanes to give 3-(4-methoxy-phenyl)-1-methyl-7-phenylamino-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidine-2-one as an off-white solid. (Yield 76.0 mg, 98.7%).

Workup

temperatureAfter cooling
washthe reaction mixture was washed with hexanes (100 mL×4)
customthe crude product was re-crystallized from ethyl acetate-hexanes

Sources & evidence

ORD record: ord-686aec9e82b648bb9716aeee2a571ef5
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07115740B2

Reaction notes

Loading…