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

HRID 605163Notes

Reaction equation

HRID 605163 reaction equation
[C:1]([C:3]1[C:4]([N:10]=[CH:11][N:12](C)C)=[N:5][C:6]([CH3:9])=[CH:7][CH:8]=1)#[N:2].N[C:16]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:17]=1[S:25][C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=1>C(O)(=O)C>[CH3:9][C:6]1[CH:7]=[CH:8][C:3]2[C:1]([NH:2][C:18]3[CH:19]=[C:20]([N+:22]([O-:24])=[O:23])[CH:21]=[CH:16][C:17]=3[S:25][C:26]3[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=3)=[N:12][CH:11]=[N:10][C:4]=2[N:5]=1

Participants

4

Reactant 2

HCID 668084214-(2-Amino-4-nitro-phenylsulfanyl)-phenolHCID 66808573N'-(3-Cyano-6-methyl-pyridin-2-yl)-N,N-dimethyl-formamidine

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of the product from Example 9B (340 mg, 1.80 mmol), and 4-(2-Amino-4-nitro-phenylsulfanyl)-phenol (480 mg, 1.80 mmol) in acetic acid (10 mL) was stirred in an oil bath preheated to 130° C. for 30 minutes. The mixture was then cooled to room temperature, the acetic acid removed under vacuum leaving a brown oil (4-[2-(7-Methyl-pyrido[2,3-d]pyrimidin-4-ylamino)-4-nitro-phenylsulfanyl]-phenol) (0.65 g, 89%).

Workup

  1. customthe acetic acid removed under vacuum

Sources & evidence

ORD record
ord-553dd8c415ca4e1fb5de01856c4f8e3f
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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