alpha-Chlorohydrin, (+)- → 3-{2-Ethyl-4-[5-(2-isopropylamino-6-methyl-pyrimidin-4-yl)-oxazol-2-yl]-6-methyl-phenoxy}-propane-1,2-diol

HRID 2069474Notes

Reaction equation

HRID 2069474 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([C:9]2[O:10][C:11]([C:14]3[CH:19]=[C:18]([CH3:20])[N:17]=[C:16]([NH:21][CH:22]([CH3:24])[CH3:23])[N:15]=3)=[CH:12][N:13]=2)[CH:6]=[C:5]([CH3:25])[C:4]=1[OH:26])[CH3:2].Cl[CH2:28][C@@H:29]([OH:32])[CH2:30][OH:31]>CC(O)C.[OH-].[Na+].CCOC(C)=O>[CH2:1]([C:3]1[CH:8]=[C:7]([C:9]2[O:10][C:11]([C:14]3[CH:19]=[C:18]([CH3:20])[N:17]=[C:16]([NH:21][CH:22]([CH3:23])[CH3:24])[N:15]=3)=[CH:12][N:13]=2)[CH:6]=[C:5]([CH3:25])[C:4]=1[O:26][CH2:28][CH:29]([OH:32])[CH2:30][OH:31])[CH3:2]

Participants

6

Reactant 2

HCID 148904alpha-Chlorohydrin, (+)-HCID 1363463712-Ethyl-4-[5-(2-isopropylamino-6-methyl-pyrimidin-4-yl)-oxazol-2-yl]-6-methyl-phenol

Product 1

HCID 685050023-{2-Ethyl-4-[5-(2-isopropylamino-6-methyl-pyrimidin-4-yl)-oxazol-2-yl]-6-methyl-phenoxy}-propane-1,2-diolYield 24.8%

Reagents, catalysts & solvents 3

HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 2-ethyl-4-[5-(2-isopropylamino-6-methyl-pyrimidin-4-yl)-oxazol-2-yl]-6-methyl-phenol (30 mg, 85 μmol) in iPrOH (4 mL), 3M aq. NaOH (1 mL) followed by (S)-3-chloro-propane-1,2-diol (67 μL, 0.85 mmol) is added. The reaction mixture is stirred at rt for 15 h, and is then diluted with EtOAc and washed with 1M aq. NaOH followed by brine. The org. solution is dried over Na2SO4, filtered and evaporated to give 3-{2-ethyl-4-[5-(2-isopropylamino-6-methyl-pyrimidin-4-yl)-oxazol-2-yl]-6-methyl-phenoxy}-propane-1,2-diol (9 mg) as a yellow solid; LC-MS: tR=0.79 min, [M+H]+=426.80.

Workup

  1. additionis added
  2. washwashed with 1M aq. NaOH
  3. dry with materialsolution is dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-64cd5bf1a110476799ce809c236d163a
Source dataset
uspto-grants-2012_10
Patent number
US08299086B2

Reaction notes

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