Water → 2-Amino-6-(4-chlorophenoxy)-4-fluoropyrimidine

HRID 1085887Notes

Reaction equation

[OH-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[NH2:11][C:12]1[N:17]=[C:16](F)[CH:15]=[C:14]([F:19])[N:13]=1.O>CO.CN1CCCC1=O>[NH2:11][C:12]1[N:13]=[C:14]([F:19])[CH:15]=[C:16]([O:10][C:7]2[CH:8]=[CH:9][C:4]([Cl:3])=[CH:5][CH:6]=2)[N:17]=1

Participants

Conditions

Temperature: 140 °C

Procedure

2.52 g (0.038 mol) of 85% sodium hydroxide were dissolved in 50 ml of methanol, 4.9 g (0.0382 mol) of 4-chlorophenol were added, and the mixture was evaporated to dryness. The residue of salt obtained in this way was taken up in 50 ml of N-methyl-2-pyrrolidone and, at 25° C., 5.0 g (0.0382 mol) of 2-amino-4,6-difluoropyrimidine were added, and the mixture was stirred at 140° C. for 4 hours. After the reaction mixture had been cooled to 25° C. it was stirred into 500 ml of water, and the resulting precipitate was isolated. 7.4 g (81% of theory) of the title compound of melting point 223°-226° C. were obtained in this way.

Workup

customthe mixture was evaporated to dryness
customThe residue of salt obtained in this way
temperatureAfter the reaction mixture had been cooled to 25° C. it
customthe resulting precipitate was isolated

Sources & evidence

ORD record: ord-7ece029aff1e468184a6961455c84fca
Source dataset: uspto-grants-1991_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05011927

Reaction notes

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