Bromine → HCID 69054306, compound

HRID 227610Notes

Reaction equation

HRID 227610 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:18]3[C:17]([NH2:19])=[N:16][CH:15]=[N:14][C:13]=3[S:12][CH:11]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[Br:20]Br>C(O)(=O)C.CN(C=O)C.C([O-])(O)=O.[Na+]>[Br:20][C:11]1[S:12][C:13]2[N:14]=[CH:15][N:16]=[C:17]([NH2:19])[C:18]=2[C:10]=1[C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1

Participants

6

Reactant 2

HCID 24408BromineHCID 597942485-(4-Nitrophenyl)thieno[2,3-d]pyrimidin-4-amine

Product 1

HCID 69054306HCID 69054306, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of Example 58C (50 mg, 0.18 mmol) in acetic acid (1 mL) and DMF (3 mL) was heated with a heat gun to obtain a clear solution, cooled to 0° C., and treated with bromine (0.02 mL). The reaction mixture was stirred at 0° C. for 1 hour, diluted with saturated NaHCO3, and filtered. The filter cake was dried to provide 56 mg of the desired product.

Workup

  1. customto obtain a clear solution
  2. filtrationfiltered
  3. customThe filter cake was dried

Sources & evidence

ORD record
ord-2ed0f528beef43c986ccabe2b2a9d6ea
Source dataset
uspto-grants-2009_07
Patent number
US07560552B2

Reaction notes

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