Potassium Carbonate → HCID 67997035, compound

HRID 45786Notes

Reaction equation

Br[C:2]1[C:3]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([C:18]#[N:19])=[CH:10][CH:9]=2)=[N:4][CH:5]=[N:6][CH:7]=1.[C:20]([O:24][CH3:25])(=[O:23])[CH2:21][SH:22].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:18]([C:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]([C:3]2[C:2]([S:22][CH2:21][C:20]([O:24][CH3:25])=[O:23])=[CH:7][N:6]=[CH:5][N:4]=2)=[CH:9][CH:10]=1)#[N:19]

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of 4-(5-bromopyrimidin-4-yl)-1-naphthonitrile (45 mg, 0.14 mmol), methyl thioglycolate (74 mg, 0.7 mmol) and potassium carbonate (27 mg, 0.2 mmol) in DMF (0.6 mL) was heated under microwave irradiation to 160° C. for 0.5 hour. The mixture was washed with water, extracted with ethyl acetate and purified by chromatography to yield methyl 2-(4-(4-cyanonaphthalen-1-yl)pyrimidin-5-ylthio)acetate (22 mg, 47%).

Workup

washThe mixture was washed with water
extractionextracted with ethyl acetate
custompurified by chromatography

Sources & evidence

ORD record: ord-cd831a4563fc4e979fdffec1e665229e
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541589B2

Reaction notes

Loading…