Water → 2-Chloro-7-iodo-5-methyl-5H-pyrrolo[3,2-d]pyrimidine

HRID 1615592노트

반응식

HRID 1615592 반응식
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[NH:10][CH:9]=[C:8]([I:11])[C:6]=2[N:7]=1.[OH-].[Na+].I[CH3:15].O>C(Cl)Cl.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[N:10]([CH3:15])[CH:9]=[C:8]([I:11])[C:6]=2[N:7]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 455884652-chloro-7-iodo-5H-pyrrolo[3,2-d]pyrimidine

생성물 1

HCID 713077402-Chloro-7-iodo-5-methyl-5H-pyrrolo[3,2-d]pyrimidine수율 70%

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 6344Dichloromethane용매

실험 절차

To a suspension of 2-chloro-7-iodo-5H-pyrrolo[3,2-d]pyrimidine (1 g, 3.57 mmol, 1.0 eq.) and NaOH (0.430 mg, 10.73 mmol, 3.0 eq.) in DCM (28 ml) was added iodomethane (0.66 g, 4.6 mmol, 1.3 eq.) and tetrabutylammonium bromide (0.116 g, 0.36 mmol, 0.1 eq.). The reaction mixture was stirred at room temperature overnight. Water was poured in and the aqueous layer extracted with ethyl acetate (2 times). The combined organic layers were then dried over Na2SO4. After filtration and evaporation the yellow residue was triturated with a mixture of ethyl acetate/petroleum spirit (1:2) to give the product as a white solid (0.73 g, 70%). 1H NMR (DMSO, 300 MHz): 8.99 (s, 1H), 8.17 (s, 1H), 3.94 (s, 3H); LRMS (EI): m/z calcd for [M+H]+ 293.93 found 294.1.

후처리

  1. extractionextracted with ethyl acetate (2 times)
  2. dry with materialThe combined organic layers were then dried over Na2SO4
  3. filtrationAfter filtration and evaporation the yellow residue
  4. customwas triturated with a mixture of ethyl acetate/petroleum spirit (1:2)

출처 및 근거

ORD 기록
ord-fe3886800d234df6b71bc76b5b67110f
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765755B2

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