4-Methoxybenzyl alcohol → 4-Chloro-6-[(4-methoxyphenyl)methoxy]-2-phenylpyrimidine

HRID 1429141Notes

Reaction equation

HRID 1429141 reaction equation
[H-].[Na+].Cl[C:4]1[CH:9]=[C:8]([Cl:10])[N:7]=[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:5]=1.[CH3:17][O:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][OH:24])=[CH:21][CH:20]=1.C([O-])(O)=O.[Na+]>C1COCC1>[Cl:10][C:8]1[CH:9]=[C:4]([O:24][CH2:23][C:22]2[CH:25]=[CH:26][C:19]([O:18][CH3:17])=[CH:20][CH:21]=2)[N:5]=[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:7]=1

Participants

6

Reactant 4

HCID 77384-Methoxybenzyl alcoholHCID 24758Sodium hydrideHCID 77338FenclorimHCID 516892Sodium Bicarbonate

Product 1

HCID 455883004-Chloro-6-[(4-methoxyphenyl)methoxy]-2-phenylpyrimidineYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

NaH (60%) (469 mg, 11.73 mmol) was added in portions to a stirred solution of 4,6-dichloro-2-phenyl-pyrimidine (2.2 g, 9.78 mmol) and 4-methoxy benzyl alcohol (1.62 mg, 11.73 mmol) in dry THF (55 ml) at 0° C. After 1.5 h, NaHCO3 (aq) was added. Some solvent was evaporated and the residue was extracted with DCM, dried (MgSO4), filtered and evaporated to give the title compound, (3.19 g, 100%), MS (M+H)+327.

Workup

  1. customSome solvent was evaporated
  2. extractionthe residue was extracted with DCM
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-ce0cfd7d03bf4e6d8676e417b42761be
Source dataset
uspto-grants-2015_01
Patent number
US08937080B2

Reaction notes

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