Dimethylformamide → N-(4-Methoxybenzyl) 4-amino-2-methylmercaptopyrimidine-5-carboxyamide

HRID 643687

Reaction equation

HRID 643687 reaction equation
[NH2:1][C:2]1[C:7]([C:8](O)=O)=[CH:6][N:5]=[C:4]([S:11][CH3:12])[N:3]=1.[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][NH2:20])=[CH:17][CH:16]=1.ON1C2C=CC=CC=2N=N1.CN(C)[CH:35]=[O:36]>>[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][NH:20][C:35]([CH2:8][C:7]2[C:2]([NH2:1])=[N:3][C:4]([S:11][CH3:12])=[N:5][CH:6]=2)=[O:36])=[CH:17][CH:16]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 754524-MethoxybenzylamineHCID 757711-HydroxybenzotriazoleHCID 221347384-Amino-2-(methylthio)pyrimidine-5-carboxylic acid

Product 1

HCID 131728064N-(4-Methoxybenzyl) 4-amino-2-methylmercaptopyrimidine-5-carboxyamideYield 81%

Procedure

To a solution of 4-amino-2-methylmercaptopyrimidine-5-carboxylic acid (185 mg, 1 mmol) and p-methoxybenzyl amine (164 mg, 1.2 mmol) in N,N-dimethylformamide was added 1-hydroxybenzotriazole (92 mg, 92 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarboiimide hydrochloride (229 mg, 1.2 mmol). The reaction mixture was stirred at room temperature over night. The solvent was removed under reduce pressure. The residue was dissolved in ethyl acetate (30 mL) and washed by water (30 mL) and brine (30 mL), dried over sodium sulfate, and the solvent was ecaporated. The residue was purified by column chromatography (hexanes:ethyl acetate=1:1) to give the desired product as a white powder (245 mg, 81%).

Workup

  1. customThe solvent was removed
  2. dissolutionThe residue was dissolved in ethyl acetate (30 mL)
  3. washwashed by water (30 mL) and brine (30 mL)
  4. dry with materialdried over sodium sulfate
  5. customThe residue was purified by column chromatography (hexanes:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-598e6ff58c9f4a9f9c8143bed7451642
Source dataset
uspto-grants-2010_04
Patent number
US07700622B2

Linked notes

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