HCID 5328418, compound → HCID 5328419, compound

HRID 394760Notes

Reaction equation

HRID 394760 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:10]3[S:17][C:16]4[C:18]([N+:22]([O-])=O)=[CH:19][CH:20]=[CH:21][C:15]=4[C:11]=3[N:12]=[CH:13][N:14]=2)[CH:5]=[CH:6][CH:7]=1>CO.[Ni]>[NH2:22][C:18]1[C:16]2[S:17][C:10]3[C:9]([NH:8][C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=4)=[N:14][CH:13]=[N:12][C:11]=3[C:15]=2[CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 1

HCID 5328418HCID 5328418, compound

Product 1

HCID 5328419HCID 5328419, compoundYield 47.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-([3-bromophenyl]amino)-6-nitrobenzothieno[3,2-d]pyrimidine (160 mg, 0.4 mmol) in methanol (10 mL) was subjected to hydrogenation with Raney Nickel (0.07 g) at 25° C. for 30 hours. After the reaction was done, the solvent was removed under reduced pressure to leave a dark brown solid. Recrystalization from wet methanol afforded 6-amino-4-([3-bromophenyl]amino)benzothieno[3,2-d]pyrimidine as a brown solid (70 mg, 43%), mp 217.6-218.8° C.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customto leave a dark brown solid
  3. customRecrystalization from wet methanol

Sources & evidence

ORD record
ord-3d16113e938f4dda89dd0f1879d2654d
Source dataset
uspto-grants-2003_08
Patent number
US06602863B1

Reaction notes

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