Dimethylformamide dimethyl acetal → 1-Dimethylamino-4-methyl-2-(2-methylsulfanyl-pyrimidin-4-yl)-pent-1-en-3-one

HRID 383726Notes

Reaction equation

[CH3:1][CH:2]([CH3:14])[C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([S:11][CH3:12])[N:6]=1.CO[CH:17](OC)[N:18]([CH3:20])[CH3:19]>C1(C)C=CC=CC=1>[CH3:17][N:18]([CH3:20])[CH:19]=[C:4]([C:5]1[CH:10]=[CH:9][N:8]=[C:7]([S:11][CH3:12])[N:6]=1)[C:3](=[O:13])[CH:2]([CH3:14])[CH3:1]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 3-methyl-1-(2-methylsulfanyl-pyrimidin-4-yl)-butan-2-one (4.3 g, 20.5 mmol) in anhydrous toluene (20 mL) is added N,N-dimethylformamide dimethylacetal (15.0 mL, 112.9 mmol). The reaction is heated at 90° C. for 4 h. The mixture is concentrated in vacuo to give the crude product, 1-dimethylamino-4-methyl-2-(2-methylsulfanyl-pyrimidin-4-yl)-pent-1-en-3-one. The crude product is used as it is.

Workup

concentrationThe mixture is concentrated in vacuo

Sources & evidence

ORD record: ord-4a49577913924a0887406bc532528031
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367687B2

Reaction notes

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