Pivalaldehyde → HCID 13072124, 화합물

HRID 1382489노트

반응식

HRID 1382489 반응식
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]

참가 물질

8

반응물 4

HCID 12417PivalaldehydeHCID 25517Ammonium ChlorideHCID 783445-BromopyrimidineHCID 178418339Butyllithium

생성물 1

HCID 13072124HCID 13072124, 화합물

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
-120 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-22e98ad2579f44e6a5f3b3db19b5069d
출처 데이터셋
uspto-grants-1989_02
특허 번호
US04806644

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