Water → HCID 178448802, compound

HRID 964850Notes

Reaction equation

HRID 964850 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH:5]=[C:4]([Cl:13])[N:3]=1.ClC1C=CC=C(C(OO)=[O:22])C=1.O>C(O)C>[NH2:1][C:2]1[N+:7]([O-:22])=[C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH:5]=[C:4]([Cl:13])[N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 229862MLS000738021

Product 1

HCID 178448802HCID 178448802, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

8.5 g of 2-amino-4-butylamino-6-chloropyrimidine are dissolved in 150 ml of ethanol. 19.95 g of meta-chloroperbenzoic acid are added dropwise as solution in 150 ml of ethanol. The reaction mixture is stirred at room temperature for 2 hours. 250 ml of water are added and ethanol is then evaporated off. The pH is adjusted to 1 with concentrated hydrochloric acid. After 1 hour's stirring, the precipitate is filtered off on sintered glass, rinsed with 50 ml of water and discarded. The pH of the solution is adjusted to 8 by adding sodium hydroxide. The mixture is extracted with 3×100 ml of dichloromethane. The organic phase is dried over sodium sulfate and then evaporated to dryness. The precipitate obtained is recrystallized from 50 ml of acetonitrile. 2.35 g of 2-amino-4-butylamino-6-chloropyrimidine 3-oxide are obtained.

Workup

  1. customethanol is then evaporated off
  2. stirringAfter 1 hour's stirring
  3. filtrationthe precipitate is filtered off on sintered glass
  4. washrinsed with 50 ml of water
  5. additionby adding sodium hydroxide
  6. extractionThe mixture is extracted with 3×100 ml of dichloromethane
  7. dry with materialThe organic phase is dried over sodium sulfate
  8. customevaporated to dryness
  9. customThe precipitate obtained
  10. customis recrystallized from 50 ml of acetonitrile

Sources & evidence

ORD record
ord-ab41da216c154c218e0fc770a0ba3ba0
Source dataset
uspto-grants-1998_06
Patent number
US05772990

Reaction notes

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