Acetonitrile → HCID 86739371, compound

HRID 1583339Notes

Reaction equation

HRID 1583339 reaction equation
[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

Participants

4

Reactant 3

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

Product 1

HCID 86739371HCID 86739371, compound

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-084be928dcde41fb9968816e283cbe78
Source dataset
uspto-grants-1985_11
Patent number
US04551457

Reaction notes

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