Phenol → 5-Fluoro-2-phenoxypyrimidin-4(3H)-one

HRID 1679356Notes

Reaction equation

[K].[C:2]1([OH:8])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:10]1[NH:15][C:14](=[O:16])[C:13]([F:17])=[CH:12][N:11]=1>C1(C)C=CC=CC=1>[O:8]([C:10]1[NH:15][C:14](=[O:16])[C:13]([F:17])=[CH:12][N:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A 11.7 g quantity of metal potassium is added to 200 ml of absolute toluene, and a mixture of 28 g of phenol and 100 ml of absolute toluene is further added dropwise to dissolve the potassium. Subsequently 14.9 g of 2-chloro-5-fluoropyrimidin-4-one is added to the solution, and the mixture is stirred at 100° C for 8 hours. The reaction mixture is thereafter treated in the same manner as in Example 6 to give 13.2 g of white crystalline 2-phenoxy-5-fluoropyrimidin-4-one in a yield of 64.1 %, m.p. 224°-225° C.

Workup

additionis further added dropwise
additionThe reaction mixture is thereafter treated in the same manner as in Example 6

Sources & evidence

ORD record: ord-56a06e48b8734d02a04673c569e0556e
Source dataset: uspto-grants-1978_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04080455

Reaction notes

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