Water → 5-(Aminomethyl)-6-(2,4-dichlorophenyl)-2-phenylpyrimidin-4-amine

HRID 983835Notes

Reaction equation

[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[Cl:17])[N:5]=[C:4]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.C(OCC)(=O)C>C1COCC1>[NH2:9][CH2:8][C:7]1[C:2]([NH2:1])=[N:3][C:4]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[N:5][C:6]=1[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=1[Cl:17]

Participants

Conditions

Temperature: 40 °C

Procedure

Under an atmosphere of argon, a solution of 4-Amino-6-(2,4-dichloro-phenyl)-2-phenyl-pyrimidine-5-carbonitrile (1.16 g, 0.34 mmol) in THF (6 ml) was added slowly to a suspension of LiAlH4 in THF (3 ml). After stirring for 2 h at 40° C., the reaction mixture was cooled to −20° C. and water (0.6 ml) was added. After 15 min, ethyl acetate was added and the mixture was filtered through Decalite. The organic phase was then separated, washed with water, and dried over sodium sulfate. Purification by flash chromatography (silica gel, methanol, dichloromethane) afforded the title compound, MS: m/e=344.2 (M+), as a light yellow solid (0.446 g, 40%).

Workup

temperaturethe reaction mixture was cooled to −20° C.
waitAfter 15 min
filtrationthe mixture was filtered through Decalite
customThe organic phase was then separated
washwashed with water
dry with materialdried over sodium sulfate
customPurification by flash chromatography (silica gel, methanol, dichloromethane)

Sources & evidence

ORD record: ord-c83a308f24654ed39f58b8b20e341877
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06867205B2

Reaction notes

Loading…