Thionyl Chloride → 6-[4-(Chloromethyl)phenyl]-N-((R)-1-phenylethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine
Reaction equation
S(Cl)([Cl:3])=O.[C:5]1([C@H:11]([NH:13][C:14]2[C:15]3[CH:22]=[C:21]([C:23]4[CH:28]=[CH:27][C:26]([CH2:29]O)=[CH:25][CH:24]=4)[NH:20][C:16]=3[N:17]=[CH:18][N:19]=2)[CH3:12])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C1(C)C=CC=CC=1>[Cl:3][CH2:29][C:26]1[CH:25]=[CH:24][C:23]([C:21]2[NH:20][C:16]3[N:17]=[CH:18][N:19]=[C:14]([NH:13][C@@H:11]([C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=4)[CH3:12])[C:15]=3[CH:22]=2)=[CH:28][CH:27]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of thionyl chloride (25.7 ml, 0.328 mol) in 180 ml of toluene is cooled to −10° C. Solid {4-[4-((R)-1-phenyl-ethylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-phenyl}-methanol (11.3 g, 0.0328 mol) is added in 8 portions over a range of 1 h. The temperature is then increased slowly to 0° C. and the mixture stirred for 2 h. The cold reaction mixture is filtered and the solid washed with toluene and ether. The crude product is suspended in water and treated with saturated sodium bicarbonate solution until the mixture turns basic. The mixture is stirred well for about 10 min and filtered. The solid is thoroughly washed with water and dried under reduced pressure to give the title compound; m.p.>320° C.; Rf (dichloromethane/ethanol 9:1)=0.46; HPLC tR=10.63 min; MS-ES+: (M+H)+=363.