Water → HCID 15516504, compound

HRID 1066053Notes

Reaction equation

HRID 1066053 reaction equation
[NH2:1][C:2]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:6](=[O:14])[N:5]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:4](=[O:21])[CH:3]=1.P(Cl)(Cl)(Cl)=O.O.[OH-].[K+].CN(C)[CH:32]=[O:33]>>[NH2:1][C:2]1[N:7]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:6](=[O:14])[N:5]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:4](=[O:21])[C:3]=1[CH:32]=[O:33]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 14797Potassium HydroxideHCID 24813Phosphorus oxychlorideHCID 10612689HCID 10612689, compound

Product 1

HCID 15516504HCID 15516504, compoundYield 40%

Procedure

A solution of 6-amino-1,3-diphenyluracil (10.0 g, 35.8 mmol) in dimethylformamide (100 mL) was cooled in an ice bath and phosphorus oxychloride (3.7 mL, 39.4 mmol) was dropped thereinto using a dropping funnel. The reaction mixture was stirred at room temperature for two hours and the reaction was stopped by adding 50 mL of water thereto. The pH was adjusted to 10 by a 1N solution of potassium hydroxide and stirring was carried out at room temperature for one additional hour. Crude crystals separated out therefrom were filtered and, after washing with 100 mL of water, the crude crystals were filtered. The resulting crude crystals were further recrystallized from hexane and ethyl acetate to give 6-amino-5-formyl-1,3-diphenyluracil (2.2 g) in a 40% yield.

Workup

  1. stirringstirring
  2. customwas carried out at room temperature for one additional hour
  3. customCrude crystals separated out
  4. filtrationtherefrom were filtered
  5. washafter washing with 100 mL of water
  6. filtrationthe crude crystals were filtered
  7. customThe resulting crude crystals were further recrystallized from hexane and ethyl acetate

Sources & evidence

ORD record
ord-d915e396d12744fd96b6983d1fc45b9e
Source dataset
uspto-grants-2001_06
Patent number
US06242452B1

Reaction notes

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