Water → HCID 178494417, compound

HRID 925992Notes

Reaction equation

HRID 925992 reaction equation
[CH3:1][O:2][C:3]1([OH:20])[CH:8]=[C:7]([O:9]C)[N:6]=[C:5]([C:11]2[S:12][CH:13]=[C:14]([C:16]([F:19])([F:18])[F:17])[N:15]=2)[NH:4]1.B(Cl)(Cl)Cl.O.C(Cl)Cl>ClCCCl>[OH:9][C:7]1[N:6]=[C:5]([C:11]2[S:12][CH:13]=[C:14]([C:16]([F:19])([F:18])[F:17])[N:15]=2)[NH:4][C:3]([O:2][CH3:1])([OH:20])[CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 25135Boron TrichlorideHCID 1784935964,6-Dimethoxy-2-(4-trifluoromethyl-thiazol-2-yl)-pyrimidin-4-ol

Product 1

HCID 178494417HCID 178494417, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of compound 288 (460 mg, 1 eq.) in DCE (10 mL) was added BCl3 (3.16 mL, 2 eq.). The mixture was stirred at 60° C. for 16 hrs. Water and DCM were then added. Organics were separated, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was triturated in a DCM/pentane mixture to yield compound 289 as a beige solid in 38% yield. MS (ESI, EI+): m/z=278 (MH+).

Workup

  1. customOrganics were separated
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was triturated in a DCM/pentane mixture

Sources & evidence

ORD record
ord-65e6bdd500a8446f8b4742946d6372e1
Source dataset
uspto-grants-2016_03
Patent number
US09284307B2

Reaction notes

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