Triphenylphosphine → HCID 20260448, compound

HRID 326148Notes

Reaction equation

HRID 326148 reaction equation
[Cl:1][CH2:2][C:3]1[N:4]=[C:5]2[S:12][CH:11]=[C:10]([C:13]3[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=3)[N:6]2[C:7](=[O:9])[CH:8]=1.[C:19]1([P:25]([C:32]2[CH:37]=[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(#N)C>[Cl-:1].[N:15]1[CH:16]=[CH:17][CH:18]=[C:13]([C:10]2[N:6]3[C:7](=[O:9])[CH:8]=[C:3]([CH2:2][P+:25]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)[N:4]=[C:5]3[S:12][CH:11]=2)[CH:14]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 13105851HCID 13105851, compound

Product 1

HCID 20260448HCID 20260448, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

7-chloromethyl-3-(3-pyridyl)-5H-thiazolo[3,2-a]pyrimidine-5-one, m.p. 280°-290° C. dec. (5.30 g), prepared according to Example 6, was reacted with triphenylphosphine (5 g) in acetonitrile (500 ml) under stirring at the reflux temperature for 40 hours. After cooling the solution was concentrated in vacuo to a small volume, diluted with isopropyl ether and the precipitate was filtered to give 8 g of [3-(3-pyridyl)-5H-thiazolo[3,2-a]pyrimidine-5-one-7-yl]methyl-triphenylphosphonium chloride, which was suspended in dimethylsulfoxide (100 ml) and treated with potassium tert-butoxide (1.66 g) dissolved in dimethylsulfoxide (50 ml) under stirring at room temperature. The solution of the ylide so obtained was reacted with 3-pyridine-carboxaldehyde (1.74 g) at room temperature for 30 minutes then the reaction mixture was diluted with ice water and neutralized with NaH2PO4.

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-a5dba1d0506a403da9da1529707a6aca
Source dataset
uspto-grants-1984_04
Patent number
US04444773

Reaction notes

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