Methanol → 3-[2-(Methylthio)-4-pyrimidinyl]-2-(3-nitrophenyl)pyrazolo[1,5-a]pyridine

HRID 1157539노트

반응식

HRID 1157539 반응식
[CH3:1][S:2][C:3]1[N:8]=[C:7]([C:9]#[C:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)[CH:6]=[CH:5][N:4]=1.[I-].[NH2:21][N+:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[OH-].[K+].CO>C(Cl)Cl.O>[CH3:1][S:2][C:3]1[N:8]=[C:7]([C:9]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=3)=[N:21][N:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=23)[CH:6]=[CH:5][N:4]=1

참가 물질

7

반응물 4

HCID 887MethanolHCID 14797Potassium HydroxideHCID 2733704Pyridinium, 1-amino-, iodide (1:1)HCID 595114132-(Methylthio)-4-[(3-nitrophenyl)ethynyl]pyrimidine

생성물 1

HCID 595114283-[2-(Methylthio)-4-pyrimidinyl]-2-(3-nitrophenyl)pyrazolo[1,5-a]pyridine

시약·촉매·용매 2

HCID 962Water용매2회HCID 6344Dichloromethane용매3회

실험 절차

To a 0° C. solution of 2-(methylthio)-4-[(3-nitrophenyl)ethynyl]pyrimidine (4.0 g, 14.7 mmol) and N-aminopyridinium iodide (6.53 g, 29.4 mmol) in DCM (150 mL) was added potassium hydroxide (2.06 g, 36.8 mmol) in water (50 mL). The reaction was allowed to warm to rt and stirred for 16 h. The mixture was diluted with DCM and water. The organic layer was separated and the aqueous layer is extracted with DCM. The combined organic layers were dried over MgSO4, filtered and concentrated to give a dark solid. The residue was dissolved in DCM and MeOH was added until the product formed as a precipitate. The product was collected by filtration and dried to supply the title compound (2.02 g) as an off-white solid. 1H NMR (400 MHz, d6-DMSO): δ 11.36 (s, 1H), 8.62 (d, 1H, J=9.2), 8.54 (d, 1H, J=5.6), 7.94 (s, 1H), 7.82 (d, 1H, J=8.8), 7.54 (t, 1H, J=8.0), 7.46 (d, 1H, J=9.2), 7.16 (d, 1H, J=5.2), 2.59 (s, 3H).

후처리

  1. customThe organic layer was separated
  2. extractionthe aqueous layer is extracted with DCM
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a dark solid
  7. customformed as a precipitate
  8. filtrationThe product was collected by filtration
  9. dry with materialdried to supply the title compound (2.02 g) as an off-white solid

출처 및 근거

ORD 기록
ord-752f0b78d9ef4a01b928fcf98459ace7
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07807673B2

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