4-(2-Amino-4-methyl-phenylsulfanyl)-phenol → 4-[4-Methyl-2-[(7-propylpyrido[2,3-d]pyrimidin-4-yl)amino]phenyl]sulfanylphenol

HRID 607240Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[S:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1.C([C:19]1[C:20]([N:28]=[CH:29][N:30]([CH3:32])C)=[N:21][C:22]([CH2:25][CH2:26][CH3:27])=[CH:23][CH:24]=1)#N>C(O)(=O)C>[CH3:8][C:6]1[CH:5]=[CH:4][C:3]([S:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[C:2]([NH:1][C:32]2[C:19]3[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][CH3:27])=[N:21][C:20]=3[N:28]=[CH:29][N:30]=2)[CH:7]=1

Participants

Conditions

Temperature: 130 °C

Procedure

The product from Example 6c (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 (77 mg, 68%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 0.96 (t, J=7.4 Hz, 3H), 1.80 (m, 2H), 1.88 (s, 6H), 2.40 (s, 3H), 2.90 (t, J=7.6 Hz, 2H), 6.74 (d, J=8.5 Hz, 2H), 6.90 (d, J=8.1 Hz, 1H), 7.03 (m, 1H), 7.18 (d, J=8.8 Hz, 2H), 7.22 (s, 1H), 7.54 (d, J=8.1 Hz, 1H), 8.53 (s, 1H), 8.78 (d, J=8.5 Hz, 1H); MS (ESI)+ m/z 403 (M+H)+.

Workup

filtrationwas collected by filtration

Sources & evidence

ORD record: ord-4e289763039c4b14a7fa6e23a120965f
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07915411B2

Reaction notes

Loading…