Thionyl Chloride → HCID 178480221, compound

HRID 474823Notes

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-7c0fd75f732d47c7a4fbe9658db846f7
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637536B2

Reaction notes

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