Diisopropylethylamine → 3-(6-Chloro-5-cyano-2-methylsulfanyl-pyrimidin-4-ylamino)-N-methoxy-4-methyl-benzamide

HRID 852030Notes

Reaction equation

HRID 852030 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([Cl:10])[N:5]=[C:4]([S:11][CH3:12])[N:3]=1.[NH2:13][C:14]1[CH:15]=[C:16]([CH:22]=[CH:23][C:24]=1[CH3:25])[C:17]([NH:19][O:20][CH3:21])=[O:18].CCN(C(C)C)C(C)C>C1COCC1>[Cl:10][C:6]1[N:5]=[C:4]([S:11][CH3:12])[N:3]=[C:2]([NH:13][C:14]2[CH:15]=[C:16]([CH:22]=[CH:23][C:24]=2[CH3:25])[C:17]([NH:19][O:20][CH3:21])=[O:18])[C:7]=1[C:8]#[N:9]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 42016204,6-Dichloro-2-(methylsulfanyl)pyrimidine-5-carbonitrileHCID 207670003-Amino-N-methoxy-4-methylbenzamide

Product 1

HCID 115741233-(6-Chloro-5-cyano-2-methylsulfanyl-pyrimidin-4-ylamino)-N-methoxy-4-methyl-benzamideYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4,6-Dichloro-2-methylsulfanyl-pyrimidine-5-carbonitrile (2.19 g, 10 mmol), 3-amino-N-methoxy-4-methyl-benzamide (1.80 g, 10 mmol) and DIEA (1.9 mL) in THF (80 mL) were stirred at room temperature for overnight. The solvent was removed in vacuo and the product (3.33 g, 92%) was obtained after purification by silica gel column chromatography.

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-27de057154b240819c6a912af4750da2
Source dataset
uspto-grants-2007_08
Patent number
US07253174B2

Reaction notes

Loading…