Water → HCID 22481942, compound

HRID 2181614Notes

Reaction equation

HRID 2181614 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH:12]([CH3:14])[NH:11][CH:10]([CH3:15])[CH2:9]2)[N:5]=[C:4]([CH:16]([O:18]C)[CH3:17])[N:3]=1.B(Br)(Br)Br.O>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:9][CH:10]([CH3:15])[NH:11][CH:12]([CH3:14])[CH2:13]2)[N:5]=[C:4]([CH:16]([OH:18])[CH3:17])[N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 22481948HCID 22481948, compound

Product 1

HCID 22481942HCID 22481942, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice-cold solution of 2-chloro-4-(3,5-dimethyl-piperazin-1-yl)-6-(1-methoxy-ethyl)-[1,3,5]triazine, prepared in Example 2 above, (2.2 mmol, 631 mg) in methylene chloride (7 mL) was added boron tribromide (1 M in methylene chloride, 11.04 mmol, 11 mL) and the reaction was stirred for 2 h. After the reaction was allowed to come to room temperature, methylene chloride (10 mL) was added to it followed by a small quantity of water (1 mL) to quench the unreacted boron tribromide. Sufficient saturated aq. sodium bicarbonate was added to raise the pH of the reaction solution to 8. The methylene chloride layer was collected, dried, filtered and the filtrate was evaporated to dryness to obtain a residue, which was purified by silica gel chromatography (eluent, 98:2 methylene chloride-methanol) to obtain 1-[4-chloro-6-(3,5-dimethyl-piperazin-1-yl)-[1,3,5]triazin-2-yl]-ethanol (65%, 392 mg); mp 126-128° C.

Workup

  1. customto come to room temperature
  2. customto quench the unreacted boron tribromide
  3. additionSufficient saturated aq. sodium bicarbonate was added
  4. temperatureto raise the pH of the reaction solution to 8
  5. customThe methylene chloride layer was collected
  6. customdried
  7. filtrationfiltered
  8. customthe filtrate was evaporated to dryness
  9. customto obtain a residue, which
  10. customwas purified by silica gel chromatography (eluent, 98:2 methylene chloride-methanol)

Sources & evidence

ORD record
ord-27eb12b462c249f39edb9855355ab0e7
Source dataset
uspto-grants-2005_05
Patent number
US06894047B2

Reaction notes

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