Sodium Nitrite → HCID 90403086, compound

HRID 2200611Notes

Reaction equation

HRID 2200611 reaction equation
[NH2:1][C:2]1[N:7]([CH3:8])[C:6](=[O:9])[N:5]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[C:4](=[O:19])[CH:3]=1.[N:20]([O-])=[O:21].[Na+]>O.C(O)(=O)C>[NH2:1][C:2]1[N:7]([CH3:8])[C:6](=[O:9])[N:5]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[C:4](=[O:19])[C:3]=1[N:20]=[O:21]

Participants

5

Reactant 2

HCID 23668193Sodium NitriteHCID 90403227HCID 90403227, compound

Product 1

HCID 90403086HCID 90403086, compoundYield 85.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 6-amino-3-(4-methoxybenzyl)-1-methylpyrimidine-2,4(1H,3H)-dione (4.3 g, 16.45 mmol) in water (20 mL) and acetic acid (20 mL) was added sodium nitrite (3.4 g, 49.4 mmol) in small portions at 70° C. After addition, the mixture was stirred at 70° C. for 4 h. The reaction was cooled and concentrated. The solids were collected, washed with water and dried under vacuum to give 6-amino-3-(4-methoxybenzyl)-1-methyl-5-nitrosopyrimidine-2,4(1H,3H)-dione (4.1 g, 85.9% yield) as purple solid. LCMS retention time 0.885 min; LCMS MH+ 291.

Workup

  1. additionAfter addition
  2. temperatureThe reaction was cooled
  3. concentrationconcentrated
  4. customThe solids were collected
  5. washwashed with water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-b56ba218ad5b4546a214fe28cb6654bc
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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