4-Methoxybenzyl alcohol → HCID 58128582, compound

HRID 1798826Notes

Reaction equation

HRID 1798826 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][OH:8])=[CH:5][CH:4]=1.[OH-].[K+].[Cl:13][C:14]1[CH:19]=[C:18](Cl)[N:17]=[C:16]([CH3:21])[N:15]=1>CN(C=O)C.C(OCC)(=O)C>[Cl:13][C:14]1[CH:19]=[C:18]([O:8][CH2:7][C:6]2[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[N:17]=[C:16]([CH3:21])[N:15]=1

Participants

6

Reactant 3

HCID 77384-Methoxybenzyl alcoholHCID 14797Potassium HydroxideHCID 2349974,6-Dichloro-2-methylpyrimidine

Product 1

HCID 58128582HCID 58128582, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

4-Methoxybenzyl alcohol (1.66 g, 12 mmol) was dissolved in DMF (20 mL). Potassium hydroxide (2.31 g, 36 mmol, 87%) was added and stirred at room temperature for 10 min followed by cooling to 0° C. 4,6-dichloro-2-methylpyrimidine (2.15 g, 13.2 mmol) was dissolved in DMF (4 mL) and added to the solution drop-wise. The internal temperature was controlled under 2° C. The reaction solution was kept at 0° C. for 2 h, then allowed to warm slowly to 16° C. over 1 hr. The reaction was diluted with ethyl acetate (50 mL), washed with brine (50 mL×2), dried over MgSO4, filtered and concentrated i. vac. The crude mixture was purified by chromatography on silica gel (eluting 7.7% ethyl acetate/hexane) to yield the titled compound as a colorless oil. LC-MS (M+1): 265.51, (M+23): 287.52.

Workup

  1. temperatureby cooling to 0° C
  2. additionadded to the solution drop-wise
  3. customwas controlled under 2° C
  4. waitThe reaction solution was kept at 0° C. for 2 h
  5. temperatureto warm slowly to 16° C. over 1 hr
  6. washwashed with brine (50 mL×2)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated i
  10. customThe crude mixture was purified by chromatography on silica gel (eluting 7.7% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-de0f1e5d843944c681f6ed778ecdc9f3
Source dataset
uspto-grants-2013_01
Patent number
US08343990B2

Reaction notes

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