Sodium Carbonate → [3-(5-Methylpyrimidin-2-yl)phenyl]methanol

HRID 655323Notes

Reaction equation

HRID 655323 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][C:5]([C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=2)[C:11](OC)=[O:12])=[N:6][CH:7]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C1COCC1.O.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.O>[CH3:1][C:2]1[CH:7]=[N:6][C:5]([C:8]2[CH:9]=[C:10]([CH2:11][OH:12])[CH:15]=[CH:16][CH:17]=2)=[N:4][CH:3]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 21226445Aluminium lithium hydrideHCID 21881883Oxolane--water (1/1)HCID 59484867Methyl 3-(5-methylpyrimidin-2-yl)benzoate

Product 1

HCID 59484945[3-(5-Methylpyrimidin-2-yl)phenyl]methanol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

1.65 g (7.16 mmol) of methyl 3-(5-methylpyrimidin-2-yl)benzoate, dissolved in 7 ml of THF, are added dropwise under a nitrogen atmosphere to a suspension of 272 mg (7.16 mmol) of lithium aluminium hydride in 7 ml of THF, and the mixture is stirred at room temperature for 24 h. 4 ml of a THF/water mixture (1:1) are subsequently added dropwise. A solution of 1.5 g of Na2CO3 in 4 ml of water is then added, the precipitate is filtered off with suction, and the residue is boiled with 2×THF/ethyl acetate and again filtered off with suction. The combined mother liquors are evaporated to dryness, the residue is dissolved in dichloromethane, and the solution is dried over sodium sulfate, filtered and again evaporated to dryness. The crude product is purified by column chromatography on silica gel; product: 500 mg; ESI: 201 (M+H).

Workup

  1. filtrationthe precipitate is filtered off with suction
  2. filtrationagain filtered off with suction
  3. customThe combined mother liquors are evaporated to dryness
  4. dissolutionthe residue is dissolved in dichloromethane
  5. dry with materialthe solution is dried over sodium sulfate
  6. filtrationfiltered
  7. customagain evaporated to dryness
  8. customThe crude product is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-70e52e2e1a444e3194fd10d5a7b4afe9
Source dataset
uspto-grants-2011_12
Patent number
US08071593B2

Reaction notes

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