Benzyl Alcohol → 2,4-Bis-benzyloxy-5-tert-butyl-6-chloro-pyrimidine

HRID 426129Notes

Reaction equation

HRID 426129 reaction equation
[Na].[C:2]([C:6]1[C:7](Cl)=[N:8][C:9](Cl)=[N:10][C:11]=1[Cl:12])([CH3:5])([CH3:4])[CH3:3].[CH2:15]([OH:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[CH2:15]([O:22][C:9]1[N:8]=[C:7]([O:22][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:6]([C:2]([CH3:5])([CH3:4])[CH3:3])=[C:11]([Cl:12])[N:10]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 3

HCID 244Benzyl AlcoholHCID 5360545SodiumHCID 136032625-tert-Butyl-2,4,6-trichloro-pyrimidine

Product 1

HCID 591848352,4-Bis-benzyloxy-5-tert-butyl-6-chloro-pyrimidineYield 90%

Procedure

To a stirred anhydrous benzyl alcohol (80 ml), was added pieces of sodium metal (1.73 g, 75 mmol). After the reaction completed, the mixture was cooled in an ice bath and 5-tert-Butyl-2,4,6-trichloro-pyrimidine (9 g, 37.5 mmol) was added. After 1 hr., the mixture was stirred at room temperature for overnight and evaporated in vacuo. The residue was dissolved in ethyl acetate, washed with water, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo. The crude product was purified by silica gel column chromatography (eluent, ether:hexanes (1:19)) to afford 13 g (90%) of a white solid. m.p. 96° C.; 1H NMR (200 MHz, CDCl3) δ 1.50 (9H, s), 5.37 (2H, s), 5.41 (2H, s), 7.34-7.46 (10H, m).

Workup

  1. temperaturethe mixture was cooled in an ice bath
  2. customevaporated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with water
  5. dry with materialdried with anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe crude product was purified by silica gel column chromatography (eluent, ether:hexanes (1:19))

Sources & evidence

ORD record
ord-9fb31e46765443bc9f2954c6ed27aa54
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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