Pivalaldehyde → HCID 13072124, compound

HRID 1382489Notes

Reaction equation

HRID 1382489 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[N:6][CH:7]=1.C([Li])CCC.[CH3:13][C:14]([CH3:18])([CH3:17])[CH:15]=[O:16].[Cl-].[NH4+]>O1CCCC1.CCOCC.O>[OH:16][CH:15]([C:2]1[CH:3]=[N:4][CH:5]=[N:6][CH:7]=1)[C:14]([CH3:18])([CH3:17])[CH3:13]

Participants

8

Reactant 4

HCID 12417PivalaldehydeHCID 25517Ammonium ChlorideHCID 783445-BromopyrimidineHCID 178418339Butyllithium

Product 1

HCID 13072124HCID 13072124, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-120 °C

Procedure

225 g of 5-bromopyrimidine are dissolved in 1.5 l of absolute tetrahydrofuran/1,000 ml of absolute ether and the solution is cooled to -120° C. 250 ml of 50% strength n-butyl-lithium (in n-hexane) are added dropwise at an internal temperature of -105° to -115° C. in the course of 2 hours. The mixture is subsequently stirred at this temperature for 1 hour. 309 ml of trimethylacetaldehyde are then added dropwise in the course of 2 hours. The reaction mixture is then subsequently stirred at this temperature for 4 hours. It is allowed to warm to room temperature overnight and 83 g of ammonium chloride, dissolved in a minimum amount of water, are then added. The aqueous phase is separated off and the organic phase is washed twice with saturated sodium chloride solution, dried over sodium sulphate and concentrated. After recrystallization of the residue from acetonitrile, 155 g (66% of theory) of 5-(1-hydroxy-2,2-dimethylpropyl)pyrimidine of melting point 94°-96° C. are obtained.

Workup

  1. stirringThe reaction mixture is then subsequently stirred at this temperature for 4 hours
  2. temperatureto warm to room temperature overnight
  3. additionare then added
  4. customThe aqueous phase is separated off
  5. washthe organic phase is washed twice with saturated sodium chloride solution
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated
  8. customAfter recrystallization of the residue from acetonitrile, 155 g (66% of theory) of 5-(1-hydroxy-2,2-dimethylpropyl)pyrimidine of melting point 94°-96° C.
  9. customare obtained

Sources & evidence

ORD record
ord-22e98ad2579f44e6a5f3b3db19b5069d
Source dataset
uspto-grants-1989_02
Patent number
US04806644

Reaction notes

Loading…