Hydrochloric Acid → HCID 58114009, compound

HRID 1046453Notes

Reaction equation

HRID 1046453 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[H-].[Na+].[CH3:11][Si:12]([CH3:17])([CH3:16])[CH2:13][CH2:14][OH:15].Cl>C1COCC1.O>[Cl:1][C:2]1[N:7]=[C:6]([O:15][CH2:14][CH2:13][Si:12]([CH3:17])([CH3:16])[CH3:11])[CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 180132-(Trimethylsilyl)ethanolHCID 24758Sodium hydrideHCID 775312,4-Dichloropyrimidine

Product 1

HCID 58114009HCID 58114009, compoundYield 79.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2,4-Dichloro-pyrimidine (2.00 g, 13.4 mmol) in THF (30 mL) was treated with sodium hydride (670 mg, 60% oil dispersion, 16.8 mmol) followed by 2-trimethylsilanyl-ethanol (2.01 mL, 14.1 mmol) in portions over 15 minutes. The reaction mixture was stirred for 16 hours and treated with 1 M HCl (20 mL). Water (20 mL) was added and the mixture was extracted with 1:1 ethyl acetate:hexanes (100 mL) followed by ethyl acetate (100 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated. Purification by flash chromatography (10-30% EtOAc:hexanes, 80 g column), afforded 2.45 g (79% yield) of 2-chloro-4-(2-trimethylsilanyl-ethoxy)-pyrimidine as a mixture of regioisomers.

Workup

  1. extractionthe mixture was extracted with 1:1 ethyl acetate
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by flash chromatography (10-30% EtOAc:hexanes, 80 g column)

Sources & evidence

ORD record
ord-fbf7b569f8e744b9aefbbc06735dbc46
Source dataset
uspto-grants-2013_10
Patent number
US08569302B2

Reaction notes

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