Diethyl Ether → HCID 178425980, compound

HRID 1836720Notes

Reaction equation

HRID 1836720 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[C:8]1([CH3:21])[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[C:9]=1[S:16]([O:19][NH2:20])(=[O:18])=[O:17].CCOCC>ClCCl>[C:8]1([CH3:21])[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[C:9]=1[S:16]([O-:19])(=[O:18])=[O:17].[NH2:1][CH:2]1[N:7]([NH2:20])[CH:6]=[CH:5][CH:4]=[NH+:3]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 79782-AminopyrimidineHCID 11830845O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamine

Product 1

HCID 178425980HCID 178425980, compoundYield 80.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-Aminopyrimidine (0.8 g, 8.41 mmole) in dichloromethane (16 mL) at 4 C. was treated dropwise with O-mesitylenesulfonylhydroxylamine (2.65 g, 12.3 mmole) in dichloromethane (10 mL). After stirring overnight at 4 C., ether (25 mL) was added and the mixture stored at 4 C. for 3 hr. The product was filtered out and washed with 1:1 dichloromethane/ether, (50 mL) giving 2.26 g crude product. Recrystalization from methanol/dichloromethane/ether gave 2.12 g of the title compound, mp 190-191 C. Ref.: Tamura et al., J. Heterocycl. Chem. 1975;12:107.

Workup

  1. waitfor 3 hr
  2. filtrationThe product was filtered out
  3. washwashed with 1:1 dichloromethane/ether, (50 mL)
  4. customgiving 2.26 g crude product
  5. customRecrystalization from methanol/dichloromethane/ether

Sources & evidence

ORD record
ord-1c002f2eee664dd883767bf502a1758b
Source dataset
uspto-grants-2004_08
Patent number
US06777557B2

Reaction notes

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