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

HRID 852031Notes

Reaction equation

HRID 852031 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-67e596287b574ebda46e6c823174f6f4
Source dataset
uspto-grants-2007_08
Patent number
US07253174B2

Reaction notes

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