Benzyl Alcohol → HCID 14717230, compound

HRID 1085885Notes

Reaction equation

HRID 1085885 reaction equation
[H-].[Na+].[NH2:3][C:4]1[N:9]=[C:8]([F:10])[CH:7]=[C:6](F)[N:5]=1.[CH2:12]([OH:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[NH2:3][C:4]1[N:9]=[C:8]([F:10])[CH:7]=[C:6]([O:19][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:5]=1

Participants

4

Reactant 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 12014802-Amino-4,6-difluoropyrimidine

Product 1

HCID 14717230HCID 14717230, compound

Conditions

Temperature
100 °C

Procedure

1.14 g (0.0382 mol) of 80% sodium hydride were added at 25° C. under nitrogen to 70 ml of benzyl alcohol, and this mixture was stirred at 100° C. for 30 minutes. After it had been cooled to 40° C., 5.0 g (0.0382 mol) of 2-amino-4,6-difluoropyrimidine were added, and the mixture was then stirred at 100° C. for 5 hours. After the reaction was complete, a little precipitate was filtered off, and the filtrate was concentrated under 1 mbar at a bath temperature of 150° C. The viscous residue obtained in this way was induced to crystallize by trituration with cyclohexane. 6.3 g (75.2% of theory) of the title compound of melting point 96°-98° C. were obtained after filtering off, washing with water and drying.

Workup

  1. temperatureAfter it had been cooled to 40° C.
  2. stirringthe mixture was then stirred at 100° C. for 5 hours
  3. filtrationa little precipitate was filtered off
  4. concentrationthe filtrate was concentrated under 1 mbar at a bath temperature of 150° C
  5. customThe viscous residue obtained in this way
  6. customto crystallize by trituration with cyclohexane

Sources & evidence

ORD record
ord-54f11e2dc5a84961947e25b0f280074e
Source dataset
uspto-grants-1991_04
Patent number
US05011927

Reaction notes

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