Dimethylformamide → Ethyl 4-({3-[3-({[(1,1-dimethylethyl)oxy]carbonyl}amino)propyl]phenyl}amino)-6-methyl-2-(methylthio)-5-pyrimidinecarboxylate

HRID 390043Notes

Reaction equation

HRID 390043 reaction equation
CC([N:5]([CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([NH2:18])[CH:13]=1)[C:6](=[O:8])[O-:7])(C)C.Cl[C:20]1[C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:24]([CH3:31])[N:23]=[C:22]([S:32][CH3:33])[N:21]=1.CCN([CH:40]([CH3:42])[CH3:41])C(C)C.[CH3:43]N(C=O)C>>[CH3:41][C:40]([O:7][C:6]([NH:5][CH2:9][CH2:10][CH2:11][C:12]1[CH:13]=[C:14]([NH:18][C:20]2[C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:24]([CH3:31])[N:23]=[C:22]([S:32][CH3:33])[N:21]=2)[CH:15]=[CH:16][CH:17]=1)=[O:8])([CH3:42])[CH3:43]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 22225416Ethyl 4-chloro-6-methyl-2-(methylsulfanyl)pyrimidine-5-carboxylateHCID 866541991,1-Dimethylethyl[3-(3-aminophenyl)propyl]carbamate

Product 1

HCID 58296314Ethyl 4-({3-[3-({[(1,1-dimethylethyl)oxy]carbonyl}amino)propyl]phenyl}amino)-6-methyl-2-(methylthio)-5-pyrimidinecarboxylateYield 29%

Conditions

Temperature
75 °C

Procedure

To a solution of 1,1-dimethylethyl[3-(3-aminophenyl)propyl]carbamate (390 mg, 1.558 mmol) in DMF (5 mL) were added ethyl 4-chloro-6-methyl-2-(methylthio)-5-pyrimidinecarboxylate (307 mg, 1.246 mmol) and DIEA (0.298 mL, 1.714 mmol), and the reaction mixture was stirred at 75° C. overnight. The reaction was then concentrated and the residue was purified using column chromatography (silica gel, 0% to 50% EtOAc gradient in hexane) to afford the product (210 mg, 29% yield).

Workup

  1. concentrationThe reaction was then concentrated
  2. customthe residue was purified

Sources & evidence

ORD record
ord-d5c7cda7dec54782a1da4bf527990038
Source dataset
uspto-grants-2013_02
Patent number
US08383635B2

Reaction notes

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