4-[2-(7-Methyl-pyrido[2,3-d]pyrimidin-4-ylamino)-4-nitro-phenylsulfanyl]-phenol → 4-[4-Amino-2-(7-methyl-pyrido[2,3-d]pyrimidin-4-ylamino)-phenylsulfanyl]-phenol

HRID 607211Notes

Reaction equation

HRID 607211 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[C:10]([NH:11][C:12]3[CH:17]=[C:16]([N+:18]([O-])=O)[CH:15]=[CH:14][C:13]=3[S:21][C:22]3[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=3)=[N:9][CH:8]=[N:7][C:6]=2[N:29]=1>C(O)(=O)C.[Pd]>[NH2:18][C:16]1[CH:15]=[CH:14][C:13]([S:21][C:22]2[CH:23]=[CH:24][C:25]([OH:28])=[CH:26][CH:27]=2)=[C:12]([NH:11][C:10]2[C:5]3[CH:4]=[CH:3][C:2]([CH3:1])=[N:29][C:6]=3[N:7]=[CH:8][N:9]=2)[CH:17]=1

Participants

4

Reactant 1

HCID 668083744-[2-(7-Methyl-pyrido[2,3-d]pyrimidin-4-ylamino)-4-nitro-phenylsulfanyl]-phenol

Product 1

HCID 668086124-[4-Amino-2-(7-methyl-pyrido[2,3-d]pyrimidin-4-ylamino)-phenylsulfanyl]-phenolYield 119.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A slurry of the product from Example 86A (0.19 g, 0.469 mmol) and 10% Pd/C (0.025 g) in acetic acid (3 ml) was placed under a hydrogen atmosphere with stirring for 2 hr at room temperature. The slurry was filtered and the solvent removed under vacuum leaving a brown solid as an acetate salt of the title compound (0.21 g, 91%).

Workup

  1. filtrationThe slurry was filtered
  2. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-ef4c2e1df2fa476b8e47f51188eb1f3f
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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