Boron tribromide → HCID 15550151, compound

HRID 1637713Notes

Reaction equation

HRID 1637713 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([S:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17]C)[CH:12]=2)[N:3]=1.B(Br)(Br)Br>C(Cl)Cl>[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([S:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([OH:17])[CH:12]=2)[N:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 470528HCID 470528, compound

Product 1

HCID 15550151HCID 15550151, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

4-amino-6-chloro-2-(3-methoxyphenylmethylthio)-pyrimidine (36 mg, 0.128 mmol; Cpd #39) is dissolved in methylene chloride (0.25 ml), cooled to 0° C. and treated with a solution of BBr3 (0.32 ml, 0.32 mmol, 1M in methylene chloride). The reaction is stirred at 0° C. for 20 min, then refluxed for 2 hrs. After cooling, the reaction is quenched with water, and refluxed for an additional 30 min. Upon cooling the solid is collected and purified by recrystallization from ethanol/water, mp 147.5-148.5° C.

Workup

  1. temperaturerefluxed for 2 hrs
  2. temperatureAfter cooling
  3. customthe reaction is quenched with water
  4. temperaturerefluxed for an additional 30 min
  5. temperatureUpon cooling the solid
  6. customis collected
  7. custompurified by recrystallization from ethanol/water, mp 147.5-148.5° C.

Sources & evidence

ORD record
ord-b7a910819d5845cb8a0c8cd9313b7019
Source dataset
uspto-grants-2000_03
Patent number
US06043248

Reaction notes

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