Propylamine → 6-Methyl-2-(propylamino)pyrimidine-4-carboxylic acid

HRID 2069382Notes

Reaction equation

HRID 2069382 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[C:4]([CH3:11])[N:3]=1.[CH2:12]([NH2:15])[CH2:13][CH3:14]>O1CCOCC1>[CH3:11][C:4]1[N:3]=[C:2]([NH:15][CH2:12][CH2:13][CH3:14])[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=1

Participants

4

Reactant 2

HCID 7852PropylamineHCID 105352132-Chloro-6-methylpyrimidine-4-carboxylic acid

Product 1

HCID 552689736-Methyl-2-(propylamino)pyrimidine-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 2-chloro-6-methylpyrimidine-4-carboxylic acid (100 mg, 0.58 mmol) and propylamine (0.48 mL) in dioxane (1 mL) is stirred at 70° C. for 18 h. The reaction mixture is concentrated and purified by prep. HPLC (X-Bridge) to give 6-methyl-2-propylamino-pyrimidine-4-carboxylic acid (81 mg) as a yellow crystalline solid; LC-MS: tR=0.56 min, [M+H]+=196.08; 1H NMR (D6-DMSO): δ 0.89 (t, J=7.3 Hz, 3H), 1.53 (m, 2H), 2.32 (s, 3H), 3.25 (m, 2H), 6.92 (s, 1H), 7.36 (s br, 1H), 13.2 (s br, 1H).

Workup

  1. concentrationThe reaction mixture is concentrated
  2. custompurified by prep

Sources & evidence

ORD record
ord-27dd00ca5c4e4a788be10580276e42eb
Source dataset
uspto-grants-2012_10
Patent number
US08299086B2

Reaction notes

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