Diethyl Ether → HCID 22220793, compound

HRID 1836722Notes

Reaction equation

HRID 1836722 reaction equation
[C:1]1([CH3:14])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[S:9]([O:12][NH2:13])(=[O:11])=[O:10].[NH2:15][C:16]1[N:21]=[C:20]([CH3:22])[CH:19]=[C:18]([CH3:23])[N:17]=1.CO.ClCCl.CCOCC>ClCCl>[C:1]1([CH3:14])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[S:9]([O-:12])(=[O:11])=[O:10].[NH2:13][N+:17]1[C:18]([CH3:23])=[CH:19][C:20]([CH3:22])=[N:21][C:16]=1[NH2:15]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 130212-Amino-4,6-dimethyl pyrimidineHCID 11830845O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamineHCID 21226129Dichloromethane methanol

Product 1

HCID 22220793HCID 22220793, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

O-(Mesitylenesulfonyl)hydroxylamine containing ca. 18% water (3.03 g, 2.56 g dry wt., ca. 11.9 mmole) was dissolved in dichloromethane (15 mL) and dried over Na2SO4 and filtered. This was added dropwise to a solution of 2-amino-4,6-dimethylpyrimidine (1 g, 8.12 mmole) in 1:6 methanol-dichloromethane (10.5 mL) in an ice bath with stirring. Stirring was continued at 4 C. overnight. Ether (20 mL) was added and the mixture was stirred at 4 C. for 3 hr. The crude product was filtered out and dried (2.50 g). This was dissolved in a minimum amount of methanol, filtered and reduced in volume to 10 mL under reduced pressure. The solution was diluted with dichloromethane (15 mL) and then with ether (15 mL). After stirring at room temp. for 2 hr, the title compound was collected as crystal flakes and dried (2.26 g, mp 242-243 C.).

Workup

  1. dry with materialdried over Na2SO4
  2. filtrationfiltered
  3. stirringStirring
  4. customovernight
  5. stirringthe mixture was stirred at 4 C
  6. filtrationThe crude product was filtered out
  7. customdried (2.50 g)
  8. dissolutionThis was dissolved in a minimum amount of methanol
  9. filtrationfiltered
  10. additionThe solution was diluted with dichloromethane (15 mL)
  11. stirringAfter stirring at room temp. for 2 hr
  12. customthe title compound was collected as crystal flakes
  13. customdried (2.26 g, mp 242-243 C.)

Sources & evidence

ORD record
ord-5ec819906239454b89ea534cbe56ff47
Source dataset
uspto-grants-2004_08
Patent number
US06777557B2

Reaction notes

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