4-Chlorobenzaldehyde → 6-amino-5-(4-chlorobenzylamino)-3-methylpyrimidine-2,4(1H,3H)-dione

HRID 2200541Notes

Reaction equation

HRID 2200541 reaction equation
[NH2:1][C:2]1[C:3](=[O:11])[N:4]([CH3:10])[C:5](=[O:9])[NH:6][C:7]=1[NH2:8].[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=1.C([BH3-])#N.[Na+]>O.C(O)(=O)C>[NH2:8][C:7]1[NH:6][C:5](=[O:9])[N:4]([CH3:10])[C:3](=[O:11])[C:2]=1[NH:1][CH2:17][C:16]1[CH:19]=[CH:20][C:13]([Cl:12])=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 77264-ChlorobenzaldehydeHCID 1201412SS-3364HCID 5003444Sodium cyanoborohydride

Product 1

HCID 904032716-amino-5-(4-chlorobenzylamino)-3-methylpyrimidine-2,4(1H,3H)-dioneYield 42.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a solution of 5,6-diamino-3-methylpyrimidine-2,4(1H,3H)-dione (0.8 g, 5.13 mmol) in water (10 mL) and acetic acid (0.5 mL) was added 4-chlorobenzaldehyde (0.72 g, 5.14 mmol), the mixture was stirred at room temperature for 5 h. The mixture was cooled to 0° C., sodium cyanoborohydride (0.3 g, 4.76 mmol) was added and the resulting mixture was stirred at room temperature overnight. The mixture was concentrated and filtered, and the filter cake was washed with methanol, dried in vacuo to give 6-amino-5-(4-chlorobenzylamino)-3-methylpyrimidine-2,4(1H,3H)-dione (0.6 g, 42.9% yield) as yellow solid. LCMS MH+ 281.

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. stirringthe resulting mixture was stirred at room temperature overnight
  3. concentrationThe mixture was concentrated
  4. filtrationfiltered
  5. washthe filter cake was washed with methanol
  6. customdried in vacuo

Sources & evidence

ORD record
ord-326c75503d254cf799e33f299497d0a6
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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