Phosphorus oxychloride → HCID 58169121, compound

HRID 1484870Notes

Reaction equation

[N+:1]([C:4]1[C:5](O)=[N:6][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[N:8][CH:9]=1)([O-:3])=[O:2].O=P(Cl)(Cl)[Cl:19]>>[Cl:19][C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=[C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[N:6]=1

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 178526801HCID 178526801, compound

Product 1

HCID 58169121HCID 58169121, compoundYield 79,242.797%

Procedure

A solution of 5-nitro-2-(pyridin-2-yl)pyrimidin-4-ol (1.74 g, 0.008 mmol, 1 equiv.) in POCl3 (6.12 g, 0.04 mmol, 5 equiv.) was refluxed for 3 h. Then, the mixture was poured into ice (200 g), extracted with EA (200 mL×2). The combined organic phases were evaporated to afford 4-chloro-5-nitro-2-(pyridin-2-yl)pyrimidine (1.5 g, 80%). LCMS: 237 [M+H]+.

Workup

extractionextracted with EA (200 mL×2)
customThe combined organic phases were evaporated

Sources & evidence

ORD record: ord-fc28c01aa4534469999223d5e9850caf
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422271B2

Reaction notes

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