Benzyl Alcohol → 2,4-Bis-benzyloxy-6-(3-[1,3]dioxolan-2-yl-5-methyl-phenoxy)-5-isopropyl-pyrimidine

HRID 426202Notes

Reaction equation

HRID 426202 reaction equation
[Na].Cl[C:3]1[N:8]=[C:7](Cl)[C:6]([CH:10]([CH3:12])[CH3:11])=[C:5]([O:13][C:14]2[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([CH:21]3[O:25][CH2:24][CH2:23][O:22]3)[CH:15]=2)[N:4]=1.[CH2:26]([OH:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>>[CH2:26]([O:33][C:3]1[N:8]=[C:7]([O:22][CH2:21][C:16]2[CH:17]=[CH:18][CH:19]=[CH:14][CH:15]=2)[C:6]([CH:10]([CH3:12])[CH3:11])=[C:5]([O:13][C:14]2[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([CH:21]3[O:25][CH2:24][CH2:23][O:22]3)[CH:15]=2)[N:4]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 3

HCID 244Benzyl Alcohol2×HCID 5360545SodiumHCID 591847212,4-Dichloro-6-(3-[1,3]dioxolan-2-yl-5-methyl-phenoxy)-5-isopropyl-pyrimidine

Product 1

HCID 591846532,4-Bis-benzyloxy-6-(3-[1,3]dioxolan-2-yl-5-methyl-phenoxy)-5-isopropyl-pyrimidineYield 57%

Procedure

To a stirred anhydrous benzyl alcohol (10 ml) under nitrogen atmosphere at room temperature, was added sodium metal (285 mg, 12.41 mmol). After 1 hr., 2,4-dichloro-6-(3-[1,3]dioxolan-2-yl-5-methyl-phenoxy)-5-isopropyl-pyrimidine (1.91 g, 5.17 mmol) in anhydrous benzyl alcohol (7 ml) was added. After stirring for overnight at room temperature, the mixture was evaporated in vacuo. The residue was dissolved in dichloromethane, filtered through a celite pad and the pad was washed with dichloromethane. The combined filtrate was then evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, EA:hexanes (1:10)) to afford 1.52 g (57%) of a colorless syrup. 1H NMR (200 MHz, CDCl3) δ 1.30 (6H, d, J=7.2 Hz), 2.39 (3H, s), 3.43 (1H, m), 4.02-4.13 (4H, m), 5.12 (2H, s), 5.42 (2H, s), 5.81 (1H, s), 6.92 (1H, s), 7.07 (1H, s), 7.16 (1H, s), 7.20-7.43 (10H, m).

Workup

  1. customthe mixture was evaporated in vacuo
  2. dissolutionThe residue was dissolved in dichloromethane
  3. filtrationfiltered through a celite pad
  4. washthe pad was washed with dichloromethane
  5. customThe combined filtrate was then evaporated in vacuo
  6. customthe residue was purified by silica gel column chromatography (eluent, EA:hexanes (1:10))

Sources & evidence

ORD record
ord-f5ca7d7148dd4879b3f7bd48483f6646
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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