4-(Morpholin-4-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine → 6,7-Dimethoxy-2-(4-morpholino-5,6-dihydropyrido[3,4-d]pyrimidin-7(8H)-yl)quinazolin-4(3H)-one

HRID 8717

Reaction equation

Cl[C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:4](=[CH:5][C:6]([O:15][CH3:16])=[C:7]([O:13][CH3:14])[CH:8]=2)[N:3]=1.[N:17]1([C:23]2[C:24]3[CH2:32][CH2:31][NH:30][CH2:29][C:25]=3[N:26]=[CH:27][N:28]=2)[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1>COC(O)C>[CH3:14][O:13][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][C:6]=1[O:15][CH3:16])[N:3]=[C:2]([N:30]1[CH2:31][CH2:32][C:24]3[C:23]([N:17]4[CH2:18][CH2:19][O:20][CH2:21][CH2:22]4)=[N:28][CH:27]=[N:26][C:25]=3[CH2:29]1)[NH:11][C:10]2=[O:12]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-chloro-6,7-dimethoxy-3H-quinazolin-4-one 1b (0.28 g, 1.18 mmol) and 4-morpholin-4-yl-5,6,7,8-tetrahydro-pyrido[3,4-d]pyrimidine 6a (0.26 g, 1.20 mmol) in methoxyethanol (10 mL) was heated to 100° C. with stirring for 18 h. After cooling to room temperature, the precipitated solid was separated by filtration, washed with methoxyethanol and dried to give 0.31 g of 6,7-dimethoxy-2-(4-morpholin-4-yl-5,8-dihydro-6H-pyrido[3,4-d]pyrimidin-7-yl)-3H-quinazolin-4-one 201, mp. 287.7–290.4° C.

Workup

temperatureAfter cooling to room temperature
customthe precipitated solid was separated by filtration
washwashed with methoxyethanol
customdried

Sources & evidence

ORD record: ord-2cf3ec24bb5345429b949a4874f9286b
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07091200B2

Linked notes

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