Dimethylamine → HCID 78322695, compound

HRID 1775671Notes

Reaction equation

Cl[CH:2]1[NH:7][C:6]2[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][S:10][C:5]=2[C:4](=[O:17])[N:3]1[C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1.[CH3:25][NH:26][CH3:27].C(N(C(C)C)CC)(C)C>C1COCC1>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([N:3]2[C:4](=[O:17])[C:5]3[S:10][CH:9]=[C:8]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)[C:6]=3[N:7]=[C:2]2[N:26]([CH3:27])[CH3:25])=[CH:19][CH:20]=1

Participants

Conditions

Temperature: 65 °C

Procedure

The thus synthesized compound 2-chloro-3-(4-chlorophenyl)-7-phenyl-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-one (22.7 mg, 0.06 mmol) was mixed with a solution of N,N-dimethylamine (3 ml) and diisopropylethylamine (0.01 ml, 0.06 mmol) in THF. The mixture was heated with stirring at 65° C. overnight. After the completion of the reaction was confirmed by TLC, the reaction mixture was cooled to room temperature and separated with water and dichloromethane. The extracted organic layer was washed with brine, dried over anhydrous MgSO4, and filtered. The filtrate was distilled under reduced pressure. The concentrate was purified by silica gel column chromatography (EtOAc:Hex=1:5) to give 14.1 mg (0.037 mmol, 62% yield) of the title compound.

Workup

temperatureThe mixture was heated
temperaturethe reaction mixture was cooled to room temperature
customseparated with water and dichloromethane
washThe extracted organic layer was washed with brine
dry with materialdried over anhydrous MgSO4
filtrationfiltered
distillationThe filtrate was distilled under reduced pressure
customThe concentrate was purified by silica gel column chromatography (EtOAc:Hex=1:5)

Sources & evidence

ORD record: ord-ee04eab3004041d0ab4727955e1de76e
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260448B2

Reaction notes

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