3-(2-Amino-4-methyl-phenylsulfanyl)-phenol → 3-[4-Methyl-2-(7-propyl-pyrido[2,3-d]pyrimidin-4-ylamino)-phenylsulfanyl]-phenol

HRID 607238Notes

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:11]=[C:12]([OH:16])[CH:13]=[CH:14][CH:15]=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:11]=[C:12]([OH:16])[CH:13]=[CH:14][CH:15]=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

3-(2-amino-4-methyl-phenylsulfanyl)-phenol (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 (78 mg, 68%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 0.95 (t, J=7.3 Hz, 3H), 1.79 (m, 2H), 1.88 (s, 6H), 2.40 (s, 3H), 2.88 (t, J=7.6 Hz, 2H), 6.57 (m, 3H), 7.00 (t, J=7.7 Hz, 1H), 7.13 (m, 1H), 7.26 (d, J=7.7 Hz, 1H), 7.38 (s, 1H), 7.51 (d, J=8.5 Hz, 1H), 8.50 (s, 1H), 8.70 (d, J=8.5 Hz, 1H); MS (ESI)+ m/z 403 (M+H)+.

Workup

filtrationwas collected by filtration

Sources & evidence

ORD record: ord-5cc75d9f96af449f8d14b10cd0e7b2a1
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07915411B2

Reaction notes

Loading…