Diisopropylethylamine → HCID 118162208, compound

HRID 1749550Notes

Reaction equation

HRID 1749550 reaction equation
[NH2:1][C@@H:2]1[CH2:5][C@H:4]([C:6]([NH2:8])=[O:7])[C:3]1([CH3:10])[CH3:9].Cl[C:12]1[C:17]([C:18]#[N:19])=[CH:16][N:15]=[C:14]([S:20][CH3:21])[N:13]=1.CCN(C(C)C)C(C)C>C(O)(C)C>[C:18]([C:17]1[C:12]([NH:1][C@@H:2]2[CH2:5][C@H:4]([C:6]([NH2:8])=[O:7])[C:3]2([CH3:10])[CH3:9])=[N:13][C:14]([S:20][CH3:21])=[N:15][CH:16]=1)#[N:19]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 131141834-Chloro-2-(methylsulfanyl)pyrimidine-5-carbonitrileHCID 118162113HCID 118162113, compound

Product 1

HCID 118162208HCID 118162208, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of (1S,3R)-3-amino-2,2-dimethylcyclobutanecarboxamide. (120 mg, crude), chloro-2-(methylthio)pyrimidine-5-carbonitrile (130 mg, 0.70 mmol) and DIEA (129 mg, 1.0 mmol) in isopropanol (5 mL) was stirred at 80° C. for 2 h. After removal of the solvent, the residue was purified by silica gel column chromatography (10%-30% ethyl acetate in petroleum ether) to afford the title compound (160 mg, 0.55 mmol, 78% yield for two steps). MS (ESI) m/z 292.2 [M+H]+.

Workup

  1. customAfter removal of the solvent
  2. customthe residue was purified by silica gel column chromatography (10%-30% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-10389be361f8404fad44374f530425e6
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

Loading…