Diethyl Ether → HCID 70522793, compound

HRID 1649479Notes

Reaction equation

HRID 1649479 reaction equation
[CH2:1]([O:3][CH2:4][CH3:5])C.[CH2:6]([Li])CCC.Br[C:12]1[CH:13]=[N:14][CH:15]=[N:16][CH:17]=1.[O:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1>>[N:14]1[CH:13]=[CH:12][CH:17]=[N:16][C:15]=1[C:19]1[C:4]([O:3][CH3:1])=[CH:5][CH:6]=[C:21]([CH2:22][OH:18])[CH:20]=1

Participants

5

Reactant 4

HCID 3283Diethyl EtherHCID 8028Tetrahydrofuran2×HCID 783445-Bromopyrimidine2×HCID 178418339Butyllithium

Product 1

HCID 70522793HCID 70522793, compound

Conditions

Temperature
-120 °C

Procedure

To a 500 ml 3-neck round bottom flask equipped with an addition funnel, septum, thermometer and an argon inlet was added 150 ml of anhydrous diethyl ether and 94 ml of 1.6 molar butyllithium solution (in hexane). The system was cooled to -120° C. and 23.85 gm of 5-bromopyrimidine in 75 ml of tetrahydrofuran was added over 2 hours. After addition of the 5-bromopyrimidine, the system was stirred for an additional 45 minutes. At this time, 18.3 ml of 4-methoxybenzyaldehyde in 75 ml of tetrahydrofuran was added to the system while still maintaining a temperature of -120° C. The system was kept at -120° C. for an additional 5 hours after addition of the 2,4-dichlorobenzyldehyde and afterwards the system was allowed to come to room temperature. After 10 hours at room temperature, the system was quenched with saturated ammonium chloride (in water). The system was adjusted to pH2 with concentrated HCl solution. The product was extracted with methylene chloride. The methylene chloride was washed with a 10% NaOH solution and then dried over sodium sulfate. The methylene chloride was removed by stripping and the residue triturated with hexane to give 12.93 gm of the 5-pyrimidyl-4-methoxyphenylcarbinol.

Workup

  1. customTo a 500 ml 3-neck round bottom flask equipped with an addition funnel
  2. temperaturewhile still maintaining a temperature of -120° C
  3. waitThe system was kept at -120° C. for an additional 5 hours
  4. additionafter addition of the 2,4-dichlorobenzyldehyde and afterwards the system
  5. customto come to room temperature
  6. waitAfter 10 hours at room temperature
  7. customthe system was quenched with saturated ammonium chloride (in water)
  8. extractionThe product was extracted with methylene chloride
  9. washThe methylene chloride was washed with a 10% NaOH solution
  10. dry with materialdried over sodium sulfate
  11. customThe methylene chloride was removed
  12. customthe residue triturated with hexane

Sources & evidence

ORD record
ord-311fd3b393c344f98cb8e61ccfd59c66
Source dataset
uspto-grants-1983_11
Patent number
US04417050

Reaction notes

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