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

HRID 1896320Notes

Reaction equation

HRID 1896320 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-6b5d1bcbc00a45dcb05b3bd18fa2ce6f
Source dataset
uspto-grants-2013_08
Patent number
US08518955B2

Reaction notes

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