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

HRID 1157539ノート

反応式

HRID 1157539 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 6344Dichloromethane溶媒3 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-752f0b78d9ef4a01b928fcf98459ace7
出典データセット
uspto-grants-2010_10
特許番号
US07807673B2

反応ノート

読み込み中…