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

HRID 1355908Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

2.22 g (12.3 mmol) guanidine carbonate was added portionwise to a stirred suspension of 0.41 g (10.3 mmol, 60% dispersion in mineral oil) sodium hydride in 20 ml DMF under argon at room temperature and stirring continued at 40° C. for 1 hour. A solution of 2.60 g (10.3 mmol) 2-(5-methyl-furan-2-carbonyl)-3,3-bis-methylsulfanyl-acrylonitrile in 10 ml DMF was then added dropwise and the reaction mixture heated at 100° C. for 1 hour. The reaction mixture was then poured onto 700 ml ice-water, and the precipitate collected by filtration, washed with water then hexane, and dried in vacuo to afford 2.38 g (94%) 2-amino-4-(5-methyl-furan-2-yl)-6-methylsulfanyl-pyrimidine-5-carbonitrile as a yellow solid. EI-MS m/e (%): 246 (M+, 64), 245 ([M—H]+, 100).

Workup

filtrationthe precipitate collected by filtration
washwashed with water
dry with materialhexane, and dried in vacuo

Sources & evidence

ORD record: ord-8b6c9821cc0b49c4bd87dfe508aa2182
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06586441B2

Reaction notes

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