Acetonitrile → HCID 86739371, 화합물

HRID 1583339노트

반응식

HRID 1583339 반응식
[Cl:1][CH2:2][C:3]1[N:4]=[C:5]2[S:12][CH:11]=[C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:6]2[C:7](=[O:9])[CH:8]=1.[C:19]1([P:25]([C:32]2C=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[C:38](#N)C>>[Cl-:1].[C:13]1([C:10]2[N:6]3[C:7](=[O:9])[CH:8]=[C:3]([C:2]4[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=4[P+:25]([CH3:38])([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[N:4]=[C:5]3[S:12][CH:11]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

참가 물질

4

반응물 3

HCID 6342AcetonitrileHCID 11776TriphenylphosphineHCID 23637467-(Chloromethyl)-3-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

생성물 1

HCID 86739371HCID 86739371, 화합물

실험 절차

7-chloromethyl-3-phenyl-5H-thiazolo[3,2-a]pyrimidine-5-one, m.p. 194°-195° C. (7.8 g), prepared according to Example 5, was reacted with triphenylphosphine (8 g) in acetonitrile (250 ml) under stirring at the reflux temperature for 24 hours. After cooling the solution was concentrated in vacuo to a small volume, diluted with isopropyl ether and the precipitate was filtered to give 11 g of [3-phenyl-5H-thiazolo[3,2-a]pyrimidine-5-one-7-yl]-methyl-triphenylphosphonium chloride, which was suspended in dimethylsulfoxide (50 ml) and treated with potassium tert-butoxide (2.46 g) dissolved in dimethylsulfoxide (50 ml) under stirring at room temperature. The solution of the ylide so obtained was reacted with 3-pyridine-carboxaldehyde (2.36 g) at room temperature for 60 minutes then the reaction mixture was diluted with ice water and neutralized with NaH2PO4. The precipitate was filtered and washed with water: crystallization from CH2Cl2 -methanol gave 2.8 g of 3-phenyl-7-trans-[ 2-(3-pyridyl)-ethenyl]-5H-thiazolo[3,2-a]pyrimidine-5-one, m.p. 270°-272° C., NMR (CDCl3) δ ppm: 6.17 (s) (1H, C-6 proton), 6.70 (s) (1H, C-2 proton), 6.97 (d) (1H, β-ethenyl proton), 7.34 (dd) (1H, C-5 pyridyl proton), 6.39 (s) (5H, phenyl protons), 7.77 (d) (1H, α-ethenyl proton), 7.87 (m) (1H, C-4 pyridyl proton), 8.54 (m) (1H, C-6 pyridyl proton), 8.80 (dd) (1H, C-2 pyridyl proton); JHαHβ =16 Hz.

후처리

  1. temperatureAfter cooling the solution
  2. concentrationwas concentrated in vacuo to a small volume
  3. additiondiluted with isopropyl ether
  4. filtrationthe precipitate was filtered

출처 및 근거

ORD 기록
ord-084be928dcde41fb9968816e283cbe78
출처 데이터셋
uspto-grants-1985_11
특허 번호
US04551457

반응 노트

불러오는 중…