2-Chloro-N4-methylpyrimidine-4,5-diamine → 2-chloro-6-(3,5-dimethoxyphenyl)-8-methylpteridin-7(8H)-one

HRID 524046

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11](=O)[C:12]([O:14]CC)=O)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[Cl:18][C:19]1[N:24]=[C:23]([NH:25][CH3:26])[C:22]([NH2:27])=[CH:21][N:20]=1>C(O)C.C(O)(=O)C.ClCCl>[Cl:18][C:19]1[N:20]=[CH:21][C:22]2[N:27]=[C:11]([C:5]3[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=3)[C:12](=[O:14])[N:25]([CH3:26])[C:23]=2[N:24]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of ethyl 2-(3,5-dimethoxyphenyl)-2-oxoacetate (1 g, 4.2 mmol) and 2-chloro-N4-methylpyrimidine-4,5-diamine (600 mg, 3.8 mmol) in ethanol (100 mL) and acetic acid (2.5 mL) was stirred at 80° C. for 48 h and cooled to RT (5° C.). The mixture was diluted with dichloromethane and washed with brine. The organic layer was directly concentrated and purified by chromatography on silica gel to give the title compound (700 mg, 50%). MS (ES+) C15H13ClN4O3 requires: 332, 334. found: 333, 335 [M+H]+.

Workup

temperaturecooled to RT (5° C.)
washwashed with brine
concentrationThe organic layer was directly concentrated
custompurified by chromatography on silica gel

Sources & evidence

ORD record: ord-c7cfbcd3f50444029c2e3d5ba79ae584
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340514B2

Linked notes

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