4-[2-(4-Fluorophenyl)ethynyl]-2-(methylthio)pyrimidine → 2-(4-fluorophenyl)-4,5-dihydro-3-[2-(methylthio)-4-pyrimidinyl]-7H-pyrazolo[1,5-c][1,3]oxazine

HRID 2063265Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]([S:16][CH3:17])[N:11]=2)=[CH:4][CH:3]=1.OC1O[N:21]=[N+:22]2[C:27]=1[CH:26]=[CH:25][O:24][CH2:23]2>C1(C)C=C(C)C=C(C)C=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:10]3[CH:15]=[CH:14][N:13]=[C:12]([S:16][CH3:17])[N:11]=3)=[C:27]3[N:22]([CH2:23][O:24][CH2:25][CH2:26]3)[N:21]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of 4-[2-(4-fluorophenyl)ethynyl]-2-(methylthio)pyrimidine (i.e. the product of Example 1, Step A) (1.26 g, 5.16 mmol) and 3-hydroxy-7H-[1,2,3]oxadiazolo[3,4-c][1,3]oxazin-8-ium inner salt (i.e. the product of Step C) (0.99 g, 6.96 mmol) in mesitylene (20 mL) was heated at 160° C. for 24 h. The reaction mixture was concentrated under reduced pressure, and the residual oil was purified by medium pressure liquid chromatography using 0-100% ethyl acetate in hexanes as eluant to give 290 mg of the title compound as a white solid.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customthe residual oil was purified by medium pressure liquid chromatography

Sources & evidence

ORD record: ord-b82dc487e4684ea18c596b9d55e936a5
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288375B2

Reaction notes

Loading…