4-Methoxybenzyl alcohol → 4-Chloro-6-(4-methoxy-benzyloxy)-2-(4-trifluoromethyl-thiazol-2-yl)pyrimidine

HRID 388704Notes

Reaction equation

HRID 388704 reaction equation
[H-].[Na+].Cl[C:4]1[CH:9]=[C:8]([Cl:10])[N:7]=[C:6]([C:11]2[S:12][CH:13]=[C:14]([C:16]([F:19])([F:18])[F:17])[N:15]=2)[N:5]=1.[CH3:20][O:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][OH:27])=[CH:24][CH:23]=1.C([O-])(O)=O.[Na+]>>[Cl:10][C:8]1[CH:9]=[C:4]([O:27][CH2:26][C:25]2[CH:28]=[CH:29][C:22]([O:21][CH3:20])=[CH:23][CH:24]=2)[N:5]=[C:6]([C:11]2[S:12][CH:13]=[C:14]([C:16]([F:19])([F:18])[F:17])[N:15]=2)[N:7]=1

Participants

5

Reactant 4

HCID 77384-Methoxybenzyl alcoholHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 582826244,6-Dichloro-2-(4-trifluoromethyl-thiazol-2-yl)-pyrimidine

Product 1

HCID 582826474-Chloro-6-(4-methoxy-benzyloxy)-2-(4-trifluoromethyl-thiazol-2-yl)pyrimidineYield 89%

Conditions

Temperature
0 °C

Procedure

NaH (60% in oil) (1.49 g, 1 eq.) was added portionwise to a stirred solution of compound 284 (11.2 g, 1 eq.) and 4-methoxybenzyl alcohol (5.15 g, 1 eq.). The reaction mixture was stirred at 0° C. for 1 hr and saturated NaHCO3 solution was added. The combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue obtained was triturated in pentane to yield compound 285 as a beige solid in 89% yield. MS (ESI, EI+): m/z=402 (MH+).

Workup

  1. dry with materialThe combined organic layers were dried over Na2SO4
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. customThe residue obtained
  5. customwas triturated in pentane

Sources & evidence

ORD record
ord-1d47d119e77440fb8bb81b055349b39f
Source dataset
uspto-grants-2013_02
Patent number
US08377962B2

Reaction notes

Loading…