5-(4-Nitrophenyl)thieno[2,3-d]pyrimidine-2,4-diamine → 5-(4-Aminophenyl)thieno[2,3-d]pyrimidine-2,4-diamine

HRID 227632

Reaction equation

HRID 227632 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][C:15]([NH2:20])=[N:14][C:13]=3[S:12][CH:11]=2)=[CH:6][CH:5]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[C:18]3[C:17]([NH2:19])=[N:16][C:15]([NH2:20])=[N:14][C:13]=3[S:12][CH:11]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 690630455-(4-Nitrophenyl)thieno[2,3-d]pyrimidine-2,4-diamine

Product 1

HCID 690629975-(4-Aminophenyl)thieno[2,3-d]pyrimidine-2,4-diamineYield 54.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of Example 337A (0.26 g) in methanol (5 mL) was stirred under a hydrogen atmosphere (balloon) in the presence of 10% Pd/C (100 mg) for 24 hours, and filtered through diatomaceous earth (Celite®). The pad was washed with methanol and the combined filtrates were concentrated and purified by silica gel chromatography with 7% methanol/dichloromethane to provide 0.127 g of the desired product. MS (ESI(+)) m/e 258 (M+H)+.

Workup

  1. filtrationfiltered through diatomaceous earth (Celite®)
  2. washThe pad was washed with methanol
  3. concentrationthe combined filtrates were concentrated
  4. custompurified by silica gel chromatography with 7% methanol/dichloromethane

Sources & evidence

ORD record
ord-6048f0f987984b829489a9f7d6e08b48
Source dataset
uspto-grants-2009_07
Patent number
US07560552B2

Linked notes

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