Triphenylphosphine → ((5-Oxo-5H-thiazolo[3,2-a]pyrimidin-7-yl)methyl)triphenylphosphoniumchloride

HRID 1642370Notes

Reaction equation

HRID 1642370 reaction equation
[Cl:1][CH2:2][C:3]1[N:4]=[C:5]2[S:12][CH:11]=[CH:10][N:6]2[C:7](=[O:9])[CH:8]=1.[C:13]1([P:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(#N)C>[Cl-:1].[O:9]=[C:7]1[N:6]2[CH:10]=[CH:11][S:12][C:5]2=[N:4][C:3]([CH2:2][P+:19]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:8]1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 20635977-(Chloromethyl)-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

Product 1

HCID 20260428((5-Oxo-5H-thiazolo[3,2-a]pyrimidin-7-yl)methyl)triphenylphosphoniumchloride

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred suspension of Step 1 intermediate (6.0 g, 29.90 mmol) in acetonitrile was added triphenylphosphine (8.6 g, 32.89 mmol) at room temperature. The resulting reaction mixture was slowly heated to reflux for 30 min. The solvent was concentrated in vacuo and the residue stirred with diisopropyl ethyl ether and filtered. The solid was dried under vacuum to afford 13.5 g of the desired compound as an off-white solid: 1H NMR (300 MHz, DMSO-d6) δ 4.96 (d, J=15.0 Hz, 2H), 6.15 (br s, 1H), 7.32 (br s, 1H), 7.60-7.74 (m, 15H), 7.86 (br s, 1H); ESI-MS (m/z) 427.33 (M+H)+.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas slowly heated
  3. temperatureto reflux for 30 min
  4. concentrationThe solvent was concentrated in vacuo
  5. filtrationfiltered
  6. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-ffe6b47e9ed8472ea6d800865271838e
Source dataset
uspto-grants-2012_02
Patent number
US08119647B2

Reaction notes

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