Pyridine → HCID 18507476, compound

HRID 1355699Notes

Reaction equation

[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=O.S(Cl)(Cl)=O.[NH2:16][C:17]1[N:22]=[C:21]([C:23]2[O:24][CH:25]=[CH:26][CH:27]=2)[C:20]([C:28]#[N:29])=[C:19]([S:30][CH3:31])[N:18]=1.N1C=CC=CC=1>ClCCl.CN(C)C=O>[C:28]([C:20]1[C:21]([C:23]2[O:24][CH:25]=[CH:26][CH:27]=2)=[N:22][C:17]([NH:16][C:9](=[O:11])[CH2:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[I:1])=[N:18][C:19]=1[S:30][CH3:31])#[N:29]

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of 338 mg (1.29 mmol) 2-iodophenylacetic acid in 5 ml dichloromethane were added dropwise 0.19 ml (2.58 mmol) thionyl chloride and one drop of N,N-dimethylformamide and the mixtured stirred at 50° C. for 2 hours. The reaction mixture was then concentrated in vacuo, protecting from moisture as much as possible, and the residue redissolved in 5 ml dichloromethane. 65 mg (0.43 mmol) 2-Amino-4-(2-furyl)-6-(methylthio)-5-pyrimidinecarbonitrile and 0.48 ml (6.0 mmol) pyridine were added and the reaction mixture stirred at room temperature for 16 hours. The reaction mixture was then concentrated in vacuo. Chromatography (dichloromethane then 5% methanol in dichloromethane) followed by trituration in ether afforded 32 mg (24%) N-(5-Cyano-4-furan-2-yl-6-methylsulfanyl-pyrimidin-2-yl)-2-(2-iodo-phenyl)-acetamide as a white crystalline solid. EI-MS m/e (%): 476 (M+, 68).

Workup

concentrationThe reaction mixture was then concentrated in vacuo
dissolutionredissolved in 5 ml dichloromethane
stirringthe reaction mixture stirred at room temperature for 16 hours
concentrationThe reaction mixture was then concentrated in vacuo

Sources & evidence

ORD record: ord-4dc6dc66319b43289a4c2f0c02e8a454
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06586441B2

Reaction notes

Loading…