Boron tribromide → HCID 11531195, compound

HRID 1766059Notes

Reaction equation

HRID 1766059 reaction equation
[C:1]([NH:5][C:6]([C:8]1[S:26][C:11]2[N:12]=[C:13]([S:24][CH3:25])[N:14]=[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([O:22]C)[CH:17]=3)[C:10]=2[C:9]=1[NH2:27])=[O:7])([CH3:4])([CH3:3])[CH3:2].B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:1]([NH:5][C:6]([C:8]1[S:26][C:11]2[N:12]=[C:13]([S:24][CH3:25])[N:14]=[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[CH:17]=3)[C:10]=2[C:9]=1[NH2:27])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 9887381Org41841

Product 1

HCID 11531195HCID 11531195, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

tert-Butyl 5-amino-2-methylthio-4-(3-methoxyphenyl)-thieno[2,3-d]pyrimidine-6-carboxamide (example 1e, 1.8 g) was dissolved in dry CH2Cl2 (30 ml) and the resulting solution was cooled down to 0° C. A solution of boron tribromide (1.28 ml) in dry CH2Cl2 (30 ml) was added dropwise and the mixture was stirred overnight at room temperature. Sat. aq. NaHCO3 was added dropwise to the reaction mixture until cessation of the exothermic reaction. Thereafter, CH2Cl2 was removed from the mixture by evaporation and a large amount of EtOAc was added. The organic layer was washed with sat. aq. NaHCO3, dried (MgSO4) and concentrated in vacuo.

Workup

  1. customThereafter, CH2Cl2 was removed from the mixture by evaporation
  2. additiona large amount of EtOAc was added
  3. washThe organic layer was washed with sat. aq. NaHCO3
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a7911500208f46019c1557b1841c299a
Source dataset
uspto-grants-2007_06
Patent number
US07229990B2

Reaction notes

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