Methanol → HCID 178447254, 화합물

HRID 1639242

반응식

HRID 1639242 반응식
[C:1]([NH:7][C:8]1[N:9]=[C:10]([OH:28])[C:11]2[CH:17]=[C:16]([C:18]#[C:19][CH2:20][O:21][CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][O:23]3)[CH:15]=[N:14][C:12]=2[N:13]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].CO.N1C2C(=CC=CC=2)C=CC=1.[H][H]>[Pd].CCOCC.C(Cl)(Cl)Cl>[C:1]([NH:7][C:8]1[N:9]=[C:10]([OH:28])[C:11]2[CH:17]=[C:16]([CH:18]=[CH:19][CH2:20][O:21][CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][O:23]3)[CH:15]=[N:14][C:12]=2[N:13]=1)(=[O:6])[C:2]([CH3:4])([CH3:5])[CH3:3]

참가 물질

8

반응물 4

HCID 887MethanolHCID 7047QuinolineHCID 178418361HCID 178418361, 화합물HCID 178447253HCID 178447253, 화합물

생성물 1

HCID 178447254HCID 178447254, 화합물수율 86.6%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 3283Diethyl Ether용매HCID 6212Chloroform용매

실험 절차

A mixture of 2 g (5.2 mm) of 2-pivaloylamino-4-hydroxy-6-(3-tetrahydropyr-2-yloxyprop-1-yn-1-yl)-pyrido[2,3-d]pyrimidine, 40 ml of methanol, 20 ml of chloroform, 40 mg of 5% palladium on barium sulfate, and 40 mg of synthetic quinoline was stirred under 1 atm hydrogen pressure for 40 min. The solvent then was removed by evaporation and the residue diluted with methylene chloride. The methylene chloride solution was filtered through silica gel with 2% methanol in methylene chloride to remove catalyst and the filtrate then concentrated to give an oil which upon adding ether yielded 1.74 g (86.6%) of 2-pivaloylamino-4-hydroxy-6-(3-tetrahydropyr-2-yloxyprop-1-en-1-yl)-pyrido[2,3-d]pyrimidine as yellow crystals which was further purified through column chromatography eluting with ethyl acetate and recrystallization using ethyl acetate. mp 166°-167° C. Analysis: Calculated for C20H26O4N4 : C, 62.16; H, 6.78; N, 14.50. Found: C, 62.30; H, 6.88; N, 14.74. NMR (CDCl3), delta, 1.35 (s, 9H), 1.54-1.88 (m, 6H), 3.51-3.58 (m, 1H), 3.85-3.93 (m, 1H), 4.26-4.33 (m, 1H), 4.51-4.57 (m, 1H), 4.70 (t, 1H, J=3.4 Hz), 6.07-6.15 (m, 1H), 6.62 (d, 1H, J=12.1 Hz), 8.35 (brs, NH), 8.37 (d, 1H, J=2.5 Hz), 8.79 (d, 1H, J=2.5 Hz), 12.7 (brs, NH).

후처리

  1. customThe solvent then was removed by evaporation
  2. additionthe residue diluted with methylene chloride
  3. filtrationThe methylene chloride solution was filtered through silica gel with 2% methanol in methylene chloride
  4. customto remove catalyst
  5. concentrationthe filtrate then concentrated
  6. customto give an oil which

출처 및 근거

ORD 기록
ord-d4022add730b48778efd33fdeb4cd853
출처 데이터셋
uspto-grants-1989_11
특허 번호
US04883799

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