Thionyl Chloride → HCID 178480221, compound

HRID 706057Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8][C:9]2[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=2)[CH:3]=1.[BH4-].[Na+].S(Cl)(Cl)=O.[CH3:23][N:24]1[CH:28]=[C:27]([CH2:29][C:30]2[C:31](=[O:37])[NH:32][C:33](=[S:36])[NH:34][CH:35]=2)[CH:26]=[N:25]1>CO.C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8][C:9]2[CH:16]=[CH:15][C:12]([CH2:13][S:36][C:33]3[NH:34][CH:35]=[C:30]([CH2:29][C:27]4[CH:26]=[N:25][N:24]([CH3:23])[CH:28]=4)[C:31](=[O:37])[N:32]=3)=[CH:11][CH:10]=2)[CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 4-[(4-chloro-2-pyridinyl)oxy]benzaldehyde (120 mg, 0.514 mmol), (which may be prepared according to procedures described in the International Patent Application Publication No. WO 199847869) in methanol (2.0 mL) was added NaBH4 (23.32 mg, 0.616 mmol). After the suspended solution turned clear, it was quenched with water. The mixture was extracted with EA and concentrated. After removing the solvent, thionyl chloride (0.187 mL, 2.57 mmol) and DCM (2 mL) was added, and stirring continued overnight. Then 5-[(1-methyl-1H-pyrazol-4-yl)methyl]-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone (114 mg, 0.514 mmol) was added. The reaction mixture was heated at 60° C. for 0.5 h. Purification via MDAP then afforded the title compound (132 mg, 58.4% yield). LCMS: rt=2.84 min, [M+H+]=440

Workup

customit was quenched with water
extractionThe mixture was extracted with EA
concentrationconcentrated
additionwas added
customPurification via MDAP

Sources & evidence

ORD record: ord-adc99a90465643dbab966f2feb989356
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174968B2

Reaction notes

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