Diisopropylethylamine → 2-(4-chloro-5-cyanopyrimidin-2-ylamino)-2-methyl-N-(2,2,2-trifluoroethyl)propanamide

HRID 40857Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([Cl:8])[C:5]([C:9]#[N:10])=[CH:4][N:3]=1.[NH2:11][C:12]([CH3:22])([CH3:21])[C:13]([NH:15][CH2:16][C:17]([F:20])([F:19])[F:18])=[O:14].CCN(C(C)C)C(C)C>C1COCC1>[Cl:8][C:6]1[C:5]([C:9]#[N:10])=[CH:4][N:3]=[C:2]([NH:11][C:12]([CH3:22])([CH3:21])[C:13]([NH:15][CH2:16][C:17]([F:18])([F:19])[F:20])=[O:14])[N:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

2,4-dichloropyrimidine-5-carbonitrile (E. F. Godefroi, J. Org. Chem., 1962, 27(6), 2264-6) (0.10 g, 0.57 mmol), 2-amino-2-methyl-N-(2,2,2-trifluoroethyl)propanamide. 1TFA (Meinke, Peter T.; Shih, Thomas L.; Fisher, Michael H., U.S. Pat. No. 6,221,894 B1) (0.171 g, 1.14 mmol) and DIPEA (0.39 mL, 2.29 mmol) were combined in anhydrous THF (5 mL) in a sealed tube and heated to 90° C. for 18 hours, before cooling to room temperature. The solvent was evaporated in vacuo and the residue purified by flash chromatography (40 g SiO2, pentane/ethyl acetate, 30-70% over 14 column volumes) to afford the title compound as a colorless waxy solid (0.036 g, 19.7%).

Workup

temperaturebefore cooling to room temperature
customThe solvent was evaporated in vacuo
customthe residue purified by flash chromatography (40 g SiO2, pentane/ethyl acetate, 30-70% over 14 column volumes)

Sources & evidence

ORD record: ord-2aa2157bda764d669d891657ea5f4da4
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530489B2

Reaction notes

Loading…