Pivalaldehyde → HCID 13072124、化合物

HRID 986469ノート

反応式

HRID 986469 の反応式
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]

参加物

8

反応物 4

HCID 12417PivalaldehydeHCID 25517Ammonium ChlorideHCID 783445-BromopyrimidineHCID 178418339Butyllithium

生成物 1

HCID 13072124HCID 13072124、化合物

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-120 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b8f1e5de8b714208b6d05cb0a8a31da7
出典データセット
uspto-grants-1987_12
特許番号
US04713456

反応ノート

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