Tetrahydrofuran → HCID 86588151, compound

HRID 1828546Notes

Reaction equation

HRID 1828546 reaction equation
C(O[CH:4]1[CH2:9][CH2:8][CH2:7][N:6]([C:10]2[N:11]=[C:12]3[CH:22]=[C:21]([CH2:23][CH2:24][C:25]4[S:26][CH:27]=[C:28]([CH:30]([CH3:32])[CH3:31])[N:29]=4)[C:20]([F:33])=[CH:19][N:13]3[C:14](=[O:18])[C:15]=2[CH:16]=O)[CH2:5]1)=O.[C:34]([O:38][C:39]([CH:41]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:40])([CH3:37])([CH3:36])[CH3:35].[O:61]1CCC[CH2:62]1>>[F:33][C:20]1[C:21]([CH2:23][CH2:24][C:25]2[S:26][CH:27]=[C:28]([CH:30]([CH3:32])[CH3:31])[N:29]=2)=[CH:22][C:12]2[N:13]([CH:19]=1)[C:14](=[O:18])[C:15](/[CH:16]=[CH:41]/[C:39]([O:38][C:34]([CH3:35])([CH3:36])[CH3:37])=[O:40])=[C:10]([N:6]1[CH2:7][CH2:8][CH2:9][CH:4]([CH:62]=[O:61])[CH2:5]1)[N:11]=2

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 256127tert-Butyl (triphenylphosphoranylidene) acetateHCID 22063510HCID 22063510, compound2×

Product 1

HCID 86588151HCID 86588151, compoundYield 84%

Procedure

The 1-{7-fluoro-3-formyl-8-[2-(4-isopropyl-1,3-thiazol-2-yl)ethyl]-4-oxo-4H-pyrido[1,2-a]pyrimidin-2-yl}-3-piperidyl formate (145 mg, 0.307 mmol) obtained in (K) was dissolved in tetrahydrofuran (5 ml), added with tert-butoxycarbonylmethylene-triphenylphosphorane (1.38 g, 3.68 mmol) and refluxed by heating for 2 days. The reaction mixture was concentrated, and the resulting residue was purified by preparative TLC (chloroform:methanol=100:4) to obtain the title compound (147 mg, 84%) as yellow solid.

Workup

  1. temperaturerefluxed
  2. temperatureby heating for 2 days
  3. concentrationThe reaction mixture was concentrated
  4. customthe resulting residue was purified by preparative TLC (chloroform:methanol=100:4)

Sources & evidence

ORD record
ord-60f4809d8ef3474ebe1286a3bee6eabb
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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