Ammonium Chloride → HCID 12882215, compound

HRID 462937Notes

Reaction equation

HRID 462937 reaction equation
[CH3:1][C:2]([CH3:14])([CH3:13])[C:3](=[O:12])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Br[C:16]1[CH:17]=[N:18][CH:19]=[N:20][CH:21]=1.C([Li])CCC.[Cl-].[NH4+]>O1CCCC1.CCOCC.CCCCCC>[CH3:1][C:2]([CH3:14])([CH3:13])[C:3]([C:16]1[CH:17]=[N:18][CH:19]=[N:20][CH:21]=1)([OH:12])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 783445-BromopyrimidineHCID 1816272-Butanone, 3,3-dimethyl-1-phenoxy-HCID 178418339Butyllithium

Product 1

HCID 12882215HCID 12882215, compoundYield 39%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-110 °C

Procedure

A solution of 19.2 g (0.1 mol) of 3,3-dimethyl-1-phenoxy-butan-2-one in 110 ml of absolute tetrahydrofuran and 70 ml of absolute ether was cooled to -120° C. under a dry nitrogen atmosphere. A solution of 15.7 g (0.1 mol) of 5-bromopyrimidine in 50 ml of absolute tetrahydrofuran was added dropwise. 60 ml of a 15% strength solution of n-butyl-lithium (containing about 0.14 mol) in n-hexane were then slowly added dropwise at -120° C. The mixture was stirred further, first for 2 hours at a temperature of about -110° C. and then overnight at -78° C. The reaction mixture was then warmed to room temperature, mixed with 100 ml of 10% strength ammonium chloride solution and concentrated in vacuo. The aqueous suspension was then extracted with ethyl acetate. The ethyl acetate extract was washed successively twice with 1N hydrochloric acid, twice with water and once with saturated sodium chloride solution, dried over sodium sulphate and concentrated. The residue was recrystallized from cyclohexane. 10.5 g (39% of theory) of 3,3-dimethyl-1-phenoxy-2-pyrimidin-5-yl-butan-2-ol of melting point 127°-129° C. were obtained.

Workup

  1. customovernight
  2. customat -78° C
  3. temperatureThe reaction mixture was then warmed to room temperature
  4. concentrationconcentrated in vacuo
  5. extractionThe aqueous suspension was then extracted with ethyl acetate
  6. extractionThe ethyl acetate extract
  7. washwas washed successively twice with 1N hydrochloric acid, twice with water and once with saturated sodium chloride solution
  8. dry with materialdried over sodium sulphate
  9. concentrationconcentrated
  10. customThe residue was recrystallized from cyclohexane

Sources & evidence

ORD record
ord-f217a0318c5b4eca81f3b24f46e2f18f
Source dataset
uspto-grants-1985_05
Patent number
US04518600

Reaction notes

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