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Phosphoric Acid → 5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-amine

HRID 1969594
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HRID 1969594 반응식
[S:1]([N:11]1[C:15]2=[N:16][CH:17]=[C:18]([NH:20]C(=O)OC(C)(C)C)[N:19]=[C:14]2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].OP(O)(O)=O.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1COCC1.O>[S:1]([N:11]1[C:15]2=[N:16][CH:17]=[C:18]([NH2:20])[N:19]=[C:14]2[CH:13]=[CH:12]1)([C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=1)(=[O:2])=[O:3]
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참가 물질

6

반응물 3

HCID 1004Phosphoric AcidHCID 62657Potassium Phosphate, TribasicHCID 580097831,1-Dimethylethyl N-(5-((4-methylphenyl)sulfonyl)-5H-pyrrolo(2,3-b)pyrazin-2-yl)carbamate

생성물 1

HCID 580099825-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-amine수율 94%

시약·촉매·용매 2

HCID 962Water용매
HCID 8028
Tetrahydrofuran
용매

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온도
65 °C

실험 절차

To a solution of tert-butyl 5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-ylcarbamate (12.35 g, 31.8 mmol, Example #3 Step E) in THF (35 mL) was added H3PO4 (20.16 mL, 350 mmol). The reaction mixture was heated to about 65° C. After about 90 min, the reaction mixture was cooled to about 0° C. and a solution of K3PO4 (29.0 mL, 350 mmol) in water (100 mL) was added. A white precipitate was removed by filtration. The organic layer was separated, dried over anhydrous MgSO4, and concd in vacuo to provide crude 5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-amine (8.58 g, 94%) as a tan solid: LC/MS (Table 1, Method a) Rt=1.85 min; MS m/z: 289 (M+H)+.

후처리

  1. temperaturethe reaction mixture was cooled to about 0° C.
  2. customA white precipitate was removed by filtration
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous MgSO4, and concd in vacuo

출처 및 근거

ORD 기록
ord-5af3242e3f8a4bb08f2a172b5d830073
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08426411B2

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