Methanol → 4-[4-Methyl-2-[(7-methylpyrido[2,3-d]pyrimidin-4-yl)amino]phenyl]sulfanylphenol

HRID 883969Notes

Reaction equation

HRID 883969 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]([CH3:22])[CH:19]=[CH:18][C:17]=1[S:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=1.CO>C(O)(=O)C>[CH3:22][C:20]1[CH:19]=[CH:18][C:17]([S:23][C:24]2[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=2)=[C:16]([NH:2][C:1]2[C:3]3[CH:8]=[CH:7][C:6]([CH3:9])=[N:5][C:4]=3[N:10]=[CH:11][N:12]=2)[CH:21]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 668081234-(2-Amino-4-methyl-phenylsulfanyl)-phenolHCID 66808573N'-(3-Cyano-6-methyl-pyridin-2-yl)-N,N-dimethyl-formamidine

Product 1

HCID 573931534-[4-Methyl-2-[(7-methylpyrido[2,3-d]pyrimidin-4-yl)amino]phenyl]sulfanylphenolYield 56%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of the product from Example 10B (100 mg, 0.575 mmol) and the product from Example 9c (146 mg, 0.632 mmol) in acetic acid (1 mL) was heated at 130° C. for 1 hour. The mixture was then allowed to cool to room temperature, then methanol (5 mL) added to the solution and the resulting solid collected and washed with methanol to provide the title compound (120 mg, 56%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 2.29 (s, 3H), 2.66 (s, 3H), 6.73 (d, J=8.8 Hz, 2H), 6.93 (m, 1H), 7.03 (m, 1H), 7.18 (d, J=8.5 Hz, 2H), 7.26, (s, 1H), 7.53 (d, J=8.5 Hz, 1H), 8.53 (s, 1H), 8.77 (m, 1H), 9.76 (bs, 1H), 9.96 (bs, 1H); MS (ESI)+ m/z 375 (M+H)+.

Workup

  1. customthe resulting solid collected
  2. washwashed with methanol

Sources & evidence

ORD record
ord-46a8f60316af41caa83c5a1db91df387
Source dataset
uspto-grants-2012_08
Patent number
US08236950B2

Reaction notes

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