4-(4-Chloro-7H-pyrrolo[2,3-D]pyrimidin-6-YL)benzoic acid ethyl ester → 4-[4-((R)-1-Phenyl-ethylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]benzoic acid ethyl ester

HRID 133023Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:21])[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[NH:20][C:14]3[N:15]=[CH:16][N:17]=[C:18](Cl)[C:13]=3[CH:12]=2)=[CH:7][CH:6]=1)[CH3:2]>C(O)CCC>[CH2:1]([O:3][C:4](=[O:21])[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[NH:20][C:14]3[N:15]=[CH:16][N:17]=[C:18]([NH:20][C@@H:11]([C:8]4[CH:9]=[CH:10][CH:5]=[CH:6][CH:7]=4)[CH3:12])[C:13]=3[CH:12]=2)=[CH:7][CH:6]=1)[CH3:2]

Participants

Conditions

Temperature: 145 °C

Procedure

1.8 g (6 mmol) 4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-benzoic acid ethyl ester (WO 97/02266) are suspended in 40 ml n-butanol and treated with 1.5 ml (12 mmol) (R)-phenethylamine. The mixture is heated to 145° C. under stirring. After 3 h a clear brown solution is obtained which is treated with a second portion of (R)-phenethylamine (0.75 ml, 6 mmol). After stirring for additional 2 h the reaction mixture is cooled in an ice bath and the title compound filtered and washed with cold n-butanol and ether; m.p. 288-290° C.; MS-ES+: (M+H)+=387.

Workup

customAfter 3 h a clear brown solution is obtained which
stirringAfter stirring for additional 2 h the reaction mixture
temperatureis cooled in an ice bath
filtrationthe title compound filtered
washwashed with cold n-butanol and ether

Sources & evidence

ORD record: ord-323b16c19b75488d8b8f97cfa6cbd902
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07390805B2

Reaction notes

Loading…