5-Methyl-2-phenylsulfanyl-phenylamine → 7-methyl-N-(5-methyl-2-phenylsulfanyl-phenyl)pyrido[2,3-d]pyrimidin-4-amine

HRID 607217Notes

Reaction equation

HRID 607217 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].[CH3:15][C:16]1[CH:17]=[CH:18][C:19]([S:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:20](N)[CH:21]=1>C(O)(=O)C>[CH3:15][C:16]1[CH:17]=[CH:18][C:19]([S:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[C:20]([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

4

Reactant 2

HCID 433496035-Methyl-2-phenylsulfanyl-phenylamineHCID 66808573N'-(3-Cyano-6-methyl-pyridin-2-yl)-N,N-dimethyl-formamidine

Product 1

HCID 574018897-methyl-N-(5-methyl-2-phenylsulfanyl-phenyl)pyrido[2,3-d]pyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of the product from Example 10B (90 mg, 0.517 mmol) and the product from Example 5I (122 mg, 0.569 mmol) in acetic acid (1 mL) was heated at 130° C. for 1 hour. The mixture was then allowed to cool to room temperature, the resulting solid collected and washed with methanol, then dissolved 50 mg of the material in dioxane (2 mL) and added hydrochloric acid followed by removal of the solvent under vacuum to provide the title compound as a hydrochloride salt. 1H NMR (300 MHz, DMSO-D6) δ ppm: 2.37 (s, 3H), 2.74 (s, 3H), 7.18 (m, 5H), 7.24 (m, 1H), 7.37 (m, 2H), 7.81 (d, J=8.5 Hz, 1H), 8.80 (s, 1H), 8.99 (d, J=8.5 Hz, 1H), 11.82 (bs, 1H); MS (ESI)+ m/z 359 (M+H)+.

Workup

  1. customthe resulting solid collected
  2. washwashed with methanol
  3. dissolutiondissolved 50 mg of the material in dioxane (2 mL)
  4. additionadded hydrochloric acid
  5. customfollowed by removal of the solvent under vacuum

Sources & evidence

ORD record
ord-84bdef5172ab4b85b9a822a37cdbf933
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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