Benzoyl Peroxide → HCID 18507253, compound

HRID 1356157Notes

Reaction equation

HRID 1356157 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[O:9][C:10]([CH3:13])=[CH:11][CH:12]=2)[C:5]([C:14]#[N:15])=[C:4]([S:16][CH3:17])[N:3]=1.[Br:18]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[O:9][C:10]([CH2:13][Br:18])=[CH:11][CH:12]=2)[C:5]([C:14]#[N:15])=[C:4]([S:16][CH3:17])[N:3]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 185073082-Amino-4-(5-methyl-furan-2-yl)-6-methylsulfanyl-pyrimidine-5-carbonitrile

Product 1

HCID 18507253HCID 18507253, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a stirred suspension of 500 mg (2.03 mmol) 2-amino-4-(5-methyl-furan-2-yl)-6-methylsulfanyl-pyrimidine-5-carbonitrile in 20 ml carbon tetrachloride under argon were added 397 mg (2.23 mmol) N-bromosuccinimide and a small spatula end of benzoyl peroxide. Stirring was continued for 8 hours while the reaction mixture was irradiated with a 500 W halogen lamp. The reaction mixture was then concentrated in vacuo. Chromatography (1/1 ethyl acetate/hexane) followed by trituration in ether afforded 250 mg (38%) 2-amino-4-(5-bromomethyl-furan-2-yl)-6-methylsulfanyl-pyrimidine-5-carbonitrile as a yellow crystalline solid. EI-MS m/e (%): 326 (M{81Br}+, 5), 325 ([M{81Br}-H]+, 6), 324 (M{79Br}+, 5), 324 ([M{79Br}-H]+, 6), 245 ([M—Br]+, 100).

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-92fe4a32d55b40c7a9854840133e07f9
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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