Sodium Hydroxide → 4-Chloro-N-(4-fluorophenyl)-5,6-dimethylpyrimidin-2-amine

HRID 1069394Notes

Reaction equation

O[C:2]1[C:7]([CH3:8])=[C:6]([CH3:9])[N:5]=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[N:3]=1.P(Cl)(Cl)([Cl:20])=O.[OH-].[Na+]>CN(C)C=O>[Cl:20][C:2]1[C:7]([CH3:8])=[C:6]([CH3:9])[N:5]=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[N:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

40.5 g (174.1 mmole) of 2-(4-fluorophenylamino)-4-hydroxy-5,6-dimethylpyrimidine produced in Example 1 was suspended in 80 ml of N,N-dimethylformamide and the resulting suspension was heated to 80° C. 31.9 g (19.4 ml, 210.1 mmole) of phosphorus oxychloride was added thereto over one hour at constant temperature of 85° C. The reaction solution was stirred for 30 minutes and then 400 g of ice-water was added thereto with stirring. The mixture was adjusted to pH 11 by adding sodium hydroxide and then the resulting solid product was filtered. The separated solid product was washed with 150 ml of 50% aqueous methanol solution and then dried to obtain 42.3 g of the title compound.

Workup

stirringwith stirring
filtrationthe resulting solid product was filtered
washThe separated solid product was washed with 150 ml of 50% aqueous methanol solution
customdried

Sources & evidence

ORD record: ord-c62cba1c5c884d44a819a00b7e24e16a
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06252076B1

Reaction notes

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