Sodium Sulfate → {3-[5-(3-Dimethylaminopropoxy)pyrimidin-2-yl]phenyl}methanol

HRID 655332Notes

Reaction equation

HRID 655332 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[CH3:11][N:12]([CH3:33])[CH2:13][CH2:14][CH2:15][O:16][C:17]1[CH:18]=[N:19][C:20]([C:23]2[CH:24]=[C:25]([CH:30]=[CH:31][CH:32]=2)[C:26](OC)=[O:27])=[N:21][CH:22]=1.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[CH3:33][N:12]([CH3:11])[CH2:13][CH2:14][CH2:15][O:16][C:17]1[CH:22]=[N:21][C:20]([C:23]2[CH:24]=[C:25]([CH2:26][OH:27])[CH:30]=[CH:31][CH:32]=2)=[N:19][CH:18]=1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 21225700DiisobutylaluminumhydrideHCID 59484848Methyl 3-[5-(3-dimethylaminopropoxy)pyrimidin-2-yl]benzoate

Product 1

HCID 59484942{3-[5-(3-Dimethylaminopropoxy)pyrimidin-2-yl]phenyl}methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

200 ml of a 1 M solution of diisobutylaluminium hydride in THF are added dropwise with stirring to a solution, kept under nitrogen, of 12.6 g (40.0 mmol) of methyl 3-[5-(3-dimethylaminopropoxy)pyrimidin-2-yl]benzoate in 200 ml of THF. After the mixture has been stirred at room temperature for 1 hour, 10 ml of a saturated aqueous sodium sulfate solution are added dropwise. The resultant precipitate is filtered off with suction and washed with dichloromethane. The filtrate is dried over sodium sulfate and evaporated. The residue is taken up in a mixture of diethyl ether and petroleum ether. The resultant precipitate is filtered off with suction, washed with petroleum ether and dried in vacuo: {3-[5-(3-dimethylaminopropoxy)pyrimidin-2-yl]phenyl}methanol as colourless crystals; m.p. 95-97° C.; ESI 288 (M+H); HPLC: Rt=2.35 min (method B).

Workup

  1. stirringAfter the mixture has been stirred at room temperature for 1 hour
  2. filtrationThe resultant precipitate is filtered off with suction
  3. washwashed with dichloromethane
  4. dry with materialThe filtrate is dried over sodium sulfate
  5. customevaporated
  6. additionThe residue is taken up in a mixture of diethyl ether and petroleum ether
  7. filtrationThe resultant precipitate is filtered off with suction
  8. washwashed with petroleum ether
  9. customdried in vacuo

Sources & evidence

ORD record
ord-b639ad1f84e14668a8bf5c1e9a671b16
Source dataset
uspto-grants-2011_12
Patent number
US08071593B2

Reaction notes

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