Tributylvinyltin → HCID 86732037, 화합물

HRID 1498777노트

반응식

HRID 1498777 반응식
Cl[C:2]1[CH:7]=[C:6]([N:8]2[C:12]([CH3:13])=[N:11][C:10]([CH3:14])=[N:9]2)[N:5]=[C:4]([S:15][CH3:16])[N:3]=1.[CH2:17]([Sn](CCCC)(CCCC)C=C)[CH2:18]CC>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:14][C:10]1[N:11]=[C:12]([CH3:13])[N:8]([C:6]2[CH:7]=[C:2]([CH:17]=[CH2:18])[N:3]=[C:4]([S:15][CH3:16])[N:5]=2)[N:9]=1

참가 물질

5

반응물 2

HCID 81998TributylvinyltinHCID 805459884-chloro-6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-(methylthio)pyrimidine

생성물 1

HCID 86732037HCID 86732037, 화합물

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매

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온도
110 °C

실험 절차

To a solution of 4-chloro-6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-(methylthio)pyrimidine (1-2) (1.01 g, 3.96 mmol, 1.0 eq.) in degassed toluene (20 mL) under nitrogen was added tetrakis(triphenylphosphine)palladium(0) (228 mg, 0.198 mmol, 0.050 eq.) followed by tributyl(vinyl)tin (1.16 mL, 3.96 mmol, 1.0 eq.) and the reaction heated to 110° C. for 2 hours. Toluene was removed by roto-evaporation and the resulting residue was purified by silica gel column chromatography (0-100% ethyl acetate in hexanes) to afford 4-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-(methylthio)-6-vinylpyrimidine (1-3) as a yellow solid. 1H NMR (300 MHz, CDCl3) δ 7.48 (s, 1H), 6.72 (dd, 1H, J=17.3, 10.3 Hz), 6.57 (dd, 1H, J=17.3, 1.4 Hz), 5.73 (dd, 1H, J=10.3, 1.4 Hz), 2.91 (s, 3H), 2.61 (s, 3H), 2.42 (s, 3H). LRMS m/z (M+H) 248 found, 248 required.

후처리

  1. customToluene was removed by roto-evaporation
  2. customthe resulting residue was purified by silica gel column chromatography (0-100% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-b66b28cc013b4c698ac5d830bd9f09d3
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09200001B2

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