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

HRID 1666073Notes

Reaction equation

HRID 1666073 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-faa72fa951d84c47a3fab840ba443309
Source dataset
uspto-grants-2011_10
Patent number
US08044040B2

Reaction notes

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