Diisopropylethylamine → 3-{5-Cyano-6-[(2,2-dimethyl-propyl)-methyl-amino]-2-methylsulfanyl-pyrimidin-4-ylamino}-N-methoxy-4-methyl-benzamide

HRID 1666074Notes

Reaction equation

HRID 1666074 reaction equation
Cl[C:2]1[N:7]=[C:6]([S:8][CH3:9])[N:5]=[C:4]([NH:10][C:11]2[CH:12]=[C:13]([CH:19]=[CH:20][C:21]=2[CH3:22])[C:14]([NH:16][O:17][CH3:18])=[O:15])[C:3]=1[C:23]#[N:24].Cl.[CH3:26][NH:27][CH2:28][C:29]([CH3:32])([CH3:31])[CH3:30].CCN(C(C)C)C(C)C>C1COCC1>[C:23]([C:3]1[C:4]([NH:10][C:11]2[CH:12]=[C:13]([CH:19]=[CH:20][C:21]=2[CH3:22])[C:14]([NH:16][O:17][CH3:18])=[O:15])=[N:5][C:6]([S:8][CH3:9])=[N:7][C:2]=1[N:27]([CH2:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH3:26])#[N:24]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 115741233-(6-Chloro-5-cyano-2-methylsulfanyl-pyrimidin-4-ylamino)-N-methoxy-4-methyl-benzamideHCID 22393520(2,2-Dimethylpropyl)(methyl)amine hydrochloride

Product 1

HCID 116976333-{5-Cyano-6-[(2,2-dimethyl-propyl)-methyl-amino]-2-methylsulfanyl-pyrimidin-4-ylamino}-N-methoxy-4-methyl-benzamideYield 44.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(6-Chloro-5-cyano-2-methylsulfanyl-pyrimidin-4-ylamino)-N-methoxy-4-methyl-benzamide (3.33 g, 9.2 mmol), N-methyl-neopentylamine hydrochloride (2.05 g, 15 mmol) and DIEA (3.87 g, 30 mmol) in THF (10 mL) were heated to 60° C. for overnight. The solvent was removed in vacuo and the product (1.75 g) was obtained after purification by silica gel column chromatography.

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-997d8b9f00204350855eee6bd751a102
Source dataset
uspto-grants-2011_10
Patent number
US08044040B2

Reaction notes

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