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Tetrabutylammonium Fluoride → N2-[4-(dimethylphosphoryl)-2-methoxyphenyl]-N4-[2-(propan-2-ylsulfonyl)phenyl]-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

HRID 921324
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HRID 921324 반응식
[CH3:1][P:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[N:13]=[C:14]([NH:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[S:36]([CH:39]([CH3:41])[CH3:40])(=[O:38])=[O:37])[C:15]3[CH:20]=[CH:19][N:18](COCC[Si](C)(C)C)[C:16]=3[N:17]=2)=[C:7]([O:42][CH3:43])[CH:6]=1)([CH3:4])=[O:3].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.C(N)CN>[CH3:4][P:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[N:13]=[C:14]([NH:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[S:36]([CH:39]([CH3:40])[CH3:41])(=[O:37])=[O:38])[C:15]3[CH:20]=[CH:19][NH:18][C:16]=3[N:17]=2)=[C:7]([O:42][CH3:43])[CH:6]=1)([CH3:1])=[O:3]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 86668794N2-[4-(dimethylphosphoryl)-2-methoxyphenyl]-N4-[2-(propan-2-ylsulfonyl)phenyl]-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

생성물 1

HCID 68166174N2-[4-(dimethylphosphoryl)-2-methoxyphenyl]-N4-[2-(propan-2-ylsulfonyl)phenyl]-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

시약·촉매·용매 2

HCID 3301Ethylenediamine용매
HCID 8028
Tetrahydrofuran
용매
2회

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온도
60 °C

실험 절차

To a solution of compound N2-[4-(dimethylphosphoryl)-2-methoxyphenyl]-N4-[2-(propan-2-ylsulfonyl)phenyl]-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine in THF (1 mL) was added tetrabutylammonium fluoride (TBAF) in THF (1.0 M, 3 mL) and ethylenediamine (0.1 mL). The solution was heated at 60° C. for 24 hrs. About 40% conversion was observed by HPLC monitoring. Volatile components were removed on rotavap and the residue was subjected to prep-HPLC purification. The desired product was determined by NMR to be contaminated with TBAF, which was removed by water wash (4 times). Evaporation of EtOAc gave the pure compound (14 mg). MS/ES+: m/z=514.

후처리

  1. customVolatile components were removed on rotavap
  2. customthe residue was subjected to prep-HPLC purification
  3. customwas removed by water
  4. washwash (4 times)
  5. customEvaporation of EtOAc

출처 및 근거

ORD 기록
ord-7ff640c87374445388c02ee9b048b583
출처 데이터셋
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09273077B2

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