Ammonium Hydroxide → HCID 90403227, compound

HRID 2200610Notes

Reaction equation

HRID 2200610 reaction equation
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]([CH2:7][N:8]2[C:13](=[O:14])[CH:12]=[C:11](/[N:15]=C/N(C)C)[N:10]([CH3:20])[C:9]2=[O:21])=[CH:5][CH:4]=1.[OH-].[NH4+]>CO>[NH2:15][C:11]1[N:10]([CH3:20])[C:9](=[O:21])[N:8]([CH2:7][C:6]2[CH:22]=[CH:23][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:13](=[O:14])[CH:12]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 90402730HCID 90402730, compound

Product 1

HCID 90403227HCID 90403227, compoundYield 66.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (E)-N′-(1-(4-methoxybenzyl)-3-methyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)-N,N-dimethylformimidamide (7.8 g, 24.7 mmol) in methanol (90 mL) was added ammonium hydroxide (155 mL, 28% wt/wt) and the mixture was stirred at room temperature for 48 h. The reaction was concentrated to give crude product which was purified by silica gel chromatography eluting with methanol/DCM (1:15) to give 6-amino-3-(4-methoxybenzyl)-1-methylpyrimidine-2,4(1H,3H)-dione (4.3 g, 66.6%) as yellow solid. LCMS retention time 0.445 min; LCMS MH+ 262.

Workup

  1. concentrationThe reaction was concentrated
  2. customto give crude product which
  3. customwas purified by silica gel chromatography
  4. washeluting with methanol/DCM (1:15)

Sources & evidence

ORD record
ord-928e1286293d46ffb2312ecb8931888b
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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