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

HRID 607237Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:6]([NH2:8])[CH:7]=1.C([C:18]1[C:19]([N:27]=[CH:28][N:29]([CH3:31])C)=[N:20][C:21]([CH2:24][CH2:25][CH3:26])=[CH:22][CH:23]=1)#N>C(O)(=O)C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[C:6]([NH:8][C:31]2[C:18]3[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH3:26])=[N:20][C:19]=3[N:27]=[CH:28][N:29]=2)[CH:7]=1

Participants

Conditions

Temperature: 130 °C

Procedure

The product from Example 5I (49 mg 0.231 mmol) and the product from Example 128A (50 mg, 0.231 mmol) were dissolved in acetic acid (1 mL) and heated to 130° C. for 1.5 hours. After cooling to room temperature a solid in the acetic acid solvent appeared which was collected by filtration to provide the title compound as an acetic acid salt (68 mg, 62%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 0.94 (t, J=7.4 Hz, 3H), 1.79 (m, 2H), 1.88 (s, 6H), 2.35 (s, 3H), 2.88 (t, J=7.6 Hz, 2H), 7.18 (m, 5H), 7.23 (m, 2H), 7.37 (s, 1H), 7.51 (d, J=8.1 Hz, 1H), 8.48 (s, 1H), 8.69 (d, J=8.5 Hz, 1H); MS (ESI)+ m/z 387 (M+H)+.

Workup

filtrationwas collected by filtration

Sources & evidence

ORD record: ord-6aa609e5086a43708f10cb6776ae8641
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07915411B2

Reaction notes

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