Methanol → HCID 178445464, compound

HRID 556376Notes

Reaction equation

HRID 556376 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH2:9][O:10][C:11](=[O:17])[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[N:4]=1.[Na+].[I-].[Si](Cl)(C)(C)C.CO>O.C(#N)C>[OH:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH2:9][O:10][C:11](=[O:17])[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[N:4]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 66992862HCID 66992862, compound

Product 1

HCID 178445464HCID 178445464, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

3.1 g (13.0 mMol) hexanoic acid 4-methoxy-pyrimidin-2-ylmethyl ester and 5.85 g (39 mMol) NaI are dissolved in 130 ml (13 mMol) of a 0.1 M solution of water in acetonitrile at 60° C. Then 4.95 ml (39 mMol) Me3SiCl are added via syringe. The resulting suspension is stirred for 7 h at 60° C. and then cooled to rt again. Then 15 ml of MeOH are added dropwise. After stirring for 10 additional minutes, the reddish suspension is concentrated in vacuo. The residue is redissolved in 300 ml EtOAc and 100 ml sat. NaHCO3 solution, the aq. layer separated off and extracted with 2×300 ml EtOAc. The organic phases are washed with 50 ml of a 0.5 M solution of Na2S2O3 and brine, dried (Na2SO4) and concentrated. Crystallization from CH2Cl2 and hexane gives the title compound: m.p.: 78° C.; MS: [M+1]+=225.

Workup

  1. temperaturecooled to rt again
  2. stirringAfter stirring for 10 additional minutes
  3. concentrationthe reddish suspension is concentrated in vacuo
  4. dissolutionThe residue is redissolved in 300 ml EtOAc
  5. custom100 ml sat. NaHCO3 solution, the aq. layer separated off
  6. extractionextracted with 2×300 ml EtOAc
  7. washThe organic phases are washed with 50 ml of a 0.5 M solution of Na2S2O3 and brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated
  10. customCrystallization from CH2Cl2 and hexane

Sources & evidence

ORD record
ord-558c15a052ef46dd9c14e24a8c2b0ccf
Source dataset
uspto-grants-2011_11
Patent number
US08058276B2

Reaction notes

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