5-Methyl-2-phenylsulfanyl-phenylamine → (5-Methyl-2-phenylsulfanyl-phenyl)-(7-propyl-pteridin-4-yl)-amine

HRID 607327Notes

Reaction equation

HRID 607327 reaction equation
[C:1]([C:3]1[C:4]([N:12]=[CH:13][N:14](C)C)=[N:5][C:6]([CH2:9][CH2:10][CH3:11])=[CH:7][N:8]=1)#[N:2].[CH3:17][C:18]1[CH:19]=[CH:20][C:21]([S:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[C:22](N)[CH:23]=1>C(O)(=O)C>[CH3:17][C:18]1[CH:19]=[CH:20][C:21]([S:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[C:22]([NH:2][C:1]2[C:3]3[C:4](=[N:5][C:6]([CH2:9][CH2:10][CH3:11])=[CH:7][N:8]=3)[N:12]=[CH:13][N:14]=2)[CH:23]=1

Participants

4

Reactant 2

HCID 433496035-Methyl-2-phenylsulfanyl-phenylamineHCID 66808636N'-(3-Cyano-6-propylpyrazin-2-yl)-N,N-dimethylformamidine

Product 1

HCID 60204835(5-Methyl-2-phenylsulfanyl-phenyl)-(7-propyl-pteridin-4-yl)-amineYield 28%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of the product from Example 243A (38.2 mg, 0.176 mmol) and the product of Example 5I (41.6 mg, 0.193 mmol, 1.1 eq) in acetic acid (1 mL) was heated under reflux for 1.5 h. The reaction mixture was cooled to room temperature and the solvent evaporated under reduced pressure. The resulting residue was triturated with methanol to provide the title compound (19 mg, 28% yield) as a beige solid. 1H NMR (300 MHz, DMSO-D6) δ ppm: 0.97 (t, J=7.35 Hz, 3H), 1.76-1.90 (m, 2H), 2.42 (s, 3H), 2.94-3.05 (m, 2H), 7.08-7.28 (m, 6H), 7.55 (d, J=8.09 Hz, 1H), 8.45 (s, 1H), 8.81 (s, 1H), 8.89 (s, 1H), 10.32 (s, 1H). MS (ESI+) m/z 388.1 (M+H)+ (ESI−) m/z 386.1 (M−H)−.

Workup

  1. temperatureunder reflux for 1.5 h
  2. customthe solvent evaporated under reduced pressure
  3. customThe resulting residue was triturated with methanol

Sources & evidence

ORD record
ord-89c6dbddf55f49dd938e60407ca0fa40
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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