Sodium hydride → 2-Amino-4-(3-methyl-furan-2-yl)-6-methylsulfanyl-pyrimidine-5-carbonitrile

HRID 1355885Notes

Reaction equation

C(=O)(O)O.[NH2:5][C:6]([NH2:8])=[NH:7].[H-].[Na+].[CH3:11][C:12]1[CH:16]=[CH:15][O:14][C:13]=1[C:17]([C:19](=[C:22](SC)[S:23][CH3:24])[C:20]#[N:21])=O>CN(C=O)C>[NH2:7][C:6]1[N:8]=[C:17]([C:13]2[O:14][CH:15]=[CH:16][C:12]=2[CH3:11])[C:19]([C:20]#[N:21])=[C:22]([S:23][CH3:24])[N:5]=1

Participants

Conditions

Temperature: 100 °C

Procedure

6.32 g (39.5 mmol) guanidine carbonate was added portionwise to a stirred suspension of 0.7 g (17.5 mmol, 60% dispersion in mineral oil) sodium hydride in 70 ml DMF under argon at room temperature and stirring continued at 40° C. for 30 minutes. A solution of 7.4 g (29.2 mmol) 2-(3-methyl-furan-2-carbonyl)-3,3-bis-methylsulfanyl-acrylonitrile in 15 ml DMF was then added dropwise and the reaction mixture heated at 100° C. for 30 minutes. The reaction mixture was then poured onto 2 l ice-water, and the precipitate collected by filtration and dried in vacuo to afford 6.12 g (85%) 2-amino-4-(3-methyl-furan-2-yl)-6-methylsulfanyl-pyrimidine-5-carbonitrile as a yellow solid. ES-MS m/e (%): 247 (M+H+, 100).

Workup

filtrationthe precipitate collected by filtration
customdried in vacuo

Sources & evidence

ORD record: ord-45fc8642f40645fe9ec2303e00835d1f
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06586441B2

Reaction notes

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