Sodium Iodide → HCID 178418757, 화합물

HRID 133155

반응식

HRID 133155 반응식
[CH:1]1[CH:2]=[CH:3][C:4]([C:7]2[N:8]=[C:9](Cl)[CH:10]=[C:11]([Cl:13])[N:12]=2)=[CH:5][CH:6]=1.[NH2:15][C:16]1[CH:20]=[C:19]([CH3:21])[NH:18][N:17]=1.C(N(CC)C(C)C)(C)C.[I-].[Na+]>C(O)CCC>[Cl:13][C:11]1[N:12]=[C:7]([C:4]2[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=2)[N:8]=[C:9]([NH:15][C:16]2[NH:17][N:18]=[C:19]([CH3:21])[CH:20]=2)[CH:10]=1

참가 물질

6

반응물 4

HCID 5238Sodium IodideHCID 77338FenclorimHCID 81531DiisopropylethylamineHCID 931461H-Pyrazol-3-amine, 5-methyl-

생성물 1

HCID 178418757HCID 178418757, 화합물수율 29.4%

시약·촉매·용매 1

HCID 2631-Butanol용매

반응 조건

온도
117 °C

실험 절차

A suspension of Fenclorim (4,6-dichloro-2-phenylpyrimidine) (0.1 g, 0.44 mmol), 3-amino-5-methylpyrazole (0.045 g, 0.47 mmol), N,N-diisopropylethylamine (0.08 ml, 0.47 mmol) and sodium iodide (0.067 g, 0.44 mmol) in n-butanol (5 ml) were heated at 117° C. for 18 hours. The solvent was removed in vacuo and the crude product purified by flash chromatography (silica gel, 3:2 Petrol:EtOAc) to afford 0.037 g (29% yield) of (6-Chloro-2-phenyl-pyrimidin-4-yl)-(5-methyl-2H-pyrazol-3-yl)-amine as a off-white solid. A suspension of the above pyrimidine (0.037 g, 0.13 mmol) and thioacetamidothiophenol (0.108 g, 0.64 mmol) in tert-butanol was heated at 85° C. under nitrogen for 2 days. The reaction mixture was cooled to room temperature and the solvent removed in vacuo. The concentrate was dissolved in EtOAc, and washed with NaHCO3 (sat, aq.). The organic layer is concentrated in vacuo, and the crude product by preperative HPLC. The residual disulfide that still remained in the mixture after HPLC may be removed by precipitation from EtOAc and filtration. The mother liquor was concentrated to afford IV-3 (7 mg, 13% yield) as an off-white solid: mp 235–236° C.; 1H NMR (DMSO) δ 2.10 (3H, s), 2.21 (3H, s), 6.33 (1H, br s), 7.50 (3H, m), 7.7–7.59 (2H, m), 7.76–7.78 (2H, m), 8.25 (2H, m), 9.72, 10.26 and 11.93 (3H, 3×br s); IR (solid) 1669, 1585, 1551, 1492, 1392, 1372, 1312, 1289, 1259, 1174, 1102, 1089, 1027, 1015, 984; MS 417.3 (M+H)+.

후처리

  1. customThe solvent was removed in vacuo
  2. customthe crude product purified by flash chromatography (silica gel, 3:2 Petrol:EtOAc)

출처 및 근거

ORD 기록
ord-db78cc694f384e1086e4d93dd92be1e6
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07390815B2

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