Lithium hydride → (2-chloropyrimidin-4-yl)(4-ethyl-1,3-thiazol-2(3H)-ylidene)acetonitrile

HRID 2375315Notes

Reaction equation

[H-].[Li+].[CH2:3]([C:5]1[N:6]=[C:7]([CH2:10][C:11]#[N:12])[S:8][CH:9]=1)[CH3:4].[Cl:13][C:14]1[N:19]=[C:18](Cl)[CH:17]=[CH:16][N:15]=1>C1COCC1>[Cl:13][C:14]1[N:19]=[C:18]([C:10](=[C:7]2[NH:6][C:5]([CH2:3][CH3:4])=[CH:9][S:8]2)[C:11]#[N:12])[CH:17]=[CH:16][N:15]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of LiH (699 mg, 87.90 mmol) in anhydrous THF was added dropwise a suspension of (4-ethyl-1,3-thiazol-2-yl)acetonitrile (6.69 g, 43.95 mmol) in THF (60 mL) and the suspension was stirred for 1 h at 0° C. A suspension of 2,4-dichloropyrimidine (7.2 g, 48.34 mmol) in THF (60 mL) was added dropwise to the pale red suspension at 0° C. and the resulting mixture was stirred at rt for 7 h. The reaction was quenched by addition water (10 mL) at 0° C. then the solution obtained was left overnight under stirring. The THF was removed under reduced pressure then 80 mL of water were added and the suspension was acidified with 1N HCl. The precipitate formed was filtered off and washed with water until neutral pH to afford 9.96 g of the title compound as a beige powder (Y=85.5%).

Workup

additionwas added dropwise
additionwas added dropwise to the pale red suspension at 0° C.
stirringthe resulting mixture was stirred at rt for 7 h
customThe reaction was quenched by addition water (10 mL) at 0° C.
customthe solution obtained
waitwas left overnight
stirringunder stirring
customThe THF was removed under reduced pressure
addition80 mL of water were added
customThe precipitate formed
filtrationwas filtered off
washwashed with water until neutral pH

Sources & evidence

ORD record: ord-377e1291196940878653e3ad12f4ca78
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07465736B2

Reaction notes

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