4-Amino-2-methyl-5-pyrimidinemethanamine → HCID 54724214, compound

HRID 1831992

Reaction equation

HRID 1831992 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])O[C:4](=[O:9])[CH:3]=1.[NH2:10][C:11]1[C:16]([CH2:17][NH2:18])=[CH:15][N:14]=[C:13]([CH3:19])[N:12]=1>O>[NH2:10][C:11]1[C:16]([CH2:17][N:18]2[C:6]([CH3:8])=[CH:7][C:2]([OH:1])=[CH:3][C:4]2=[O:9])=[CH:15][N:14]=[C:13]([CH3:19])[N:12]=1

Participants

4

Reactant 2

HCID 667624-Amino-2-methyl-5-pyrimidinemethanamineHCID 546757574-Hydroxy-6-methyl-2-pyrone

Product 1

HCID 54724214HCID 54724214, compoundYield 58.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-hydroxy-6-methyl-2-pyrone (0.9 g, 0.007 mol) and 4-amino-5-aminomethyl-2-methylpyrimidine (1.0 g, 0.007 mol) in water (10.0 ml) was heated at 100° C. for 1 h under argon atmosphere. The reaction mixture was cooled, and filtered the yellow precipitate. It was washed successively with cold water, ethanol, and dried in vacuo to afford the title compound (1.01 g, 51%) as a pale yellow powder: 1H NMR (DMSO-d6/400 MHz) δ 7.62 (s, 1H), 7.04 (s, 1H), 5.83 (d, 1H, J=2.0 Hz), 5.58 (d, 1H, J=2.0 Hz), 4.92 (s, 2H), 2.24 (s, 3H), and 2.22 (s, 3H); ES-HRMS m/z 325.0304 (M+H C12H14N4O2Br requires 325.0295). Step 2 1-[(4-amino-2-methylpyrimidin-5-yl)methyl]-3-bromo-4-hydroxy-6-methylpyridin-2(1H)-one

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered the yellow precipitate
  3. washIt was washed successively with cold water, ethanol
  4. customdried in vacuo

Sources & evidence

ORD record
ord-3dba739c2a4d4cffbeddd87551f97052
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Linked notes

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