Benzyl Alcohol → 2,4-Bis-benzyloxy-5-isopropyl-6-(2,3,5-trimethyl-phenoxy)-pyrimidine

HRID 426259Notes

Reaction equation

HRID 426259 reaction equation
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl[C:12]1[N:17]=[C:16](Cl)[C:15]([CH:19]([CH3:21])[CH3:20])=[C:14]([O:22][C:23]2[CH:28]=[C:27]([CH3:29])[CH:26]=[C:25]([CH3:30])[C:24]=2[CH3:31])[N:13]=1.C([O:35][CH2:36][CH3:37])(=O)C>CN(C=O)C>[CH2:3]([O:10][C:12]1[N:17]=[C:16]([O:35][CH2:36][C:37]2[CH:8]=[CH:9][CH:4]=[CH:5][CH:6]=2)[C:15]([CH:19]([CH3:21])[CH3:20])=[C:14]([O:22][C:23]2[CH:28]=[C:27]([CH3:29])[CH:26]=[C:25]([CH3:30])[C:24]=2[CH3:31])[N:13]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 591846652,4-Dichloro-5-isopropyl-6-(2,3,5-trimethyl-phenoxy)-pyrimidine

Product 1

HCID 591848362,4-Bis-benzyloxy-5-isopropyl-6-(2,3,5-trimethyl-phenoxy)-pyrimidineYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60%, 81 mg, 1.98 mmol. 3 eq.) was added to benzyl alcohol (205 μl, 1.98 mmol, 3 eq.) in 10 mL DMF. The mixture was stirred at room temperature for 15 minutes and then added to 2,4-dichloro-5-isopropyl-6-(2,3,5-trimethyl-phenoxy)-pyrimidine (320 mg, 0.66 mmol, 1 eq.). The reaction was heated to 70° C. for 1 hour. The reaction was cooled down to room temperature. Ethyl acetate was added and washed with brine. The organic layer was concentrated down and purified (silica gel, 0-50% EtOAC/hexane) to give white solid (260 mg, 84%). LC-MS shows 469.2 (M+1). 1H NMR (300 MHz, CDCl3): δ 7.3-7.5 (m, 10H), 6.91 (s, 1H), 6.72 (s, 1H), 5.41 (m, 4H), 3.48 (m, 1H), 2.38 (s, 6H), 2.0 (s, 3H), 1.36 (d, 6H).

Workup

  1. temperatureThe reaction was heated to 70° C. for 1 hour
  2. temperatureThe reaction was cooled down to room temperature
  3. washwashed with brine
  4. concentrationThe organic layer was concentrated down
  5. custompurified (silica gel, 0-50% EtOAC/hexane)

Sources & evidence

ORD record
ord-7076d14792db475f8ecfdcbd6e62ecbf
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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