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

HRID 883974Notes

Reaction equation

HRID 883974 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]([CH:24]2[CH2:26][CH2:25]2)=[CH:22][CH:23]=1)#N.NC1C=C(C)C=CC=1SC1C=CC(O)=CC=1.C(C1C(N=CN(C)C)=NC(C)=CC=1)#N>>[CH:24]1([C:21]2[CH:22]=[CH:23][C:18]3[C:31]([NH:8][C:6]4[CH:7]=[C:2]([CH3:1])[CH:3]=[CH:4][C:5]=4[S:9][C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=4)=[N:29][CH:28]=[N:27][C:19]=3[N:20]=2)[CH2:25][CH2:26]1

Participants

5

Reactant 4

HCID 433496035-Methyl-2-phenylsulfanyl-phenylamine2×HCID 668081234-(2-Amino-4-methyl-phenylsulfanyl)-phenolHCID 66808412N'-(3-Cyano-6-cyclopropyl-pyridin-2-yl)-N,N-dimethyl-formamidine2×HCID 66808573N'-(3-Cyano-6-methyl-pyridin-2-yl)-N,N-dimethyl-formamidine

Product 1

HCID 573913927-cyclopropyl-N-(5-methyl-2-phenylsulfanyl-phenyl)pyrido[2,3-d]pyrimidin-4-amine

Procedure

The product from Example 7f was reacted with the product from Example 77A using the procedure from Example 73 substituting the product from Example 7f for the product from Example 9c and substituting the product from Example 77A for the product from Example 10B to provide the crude residue which was purified by trituration with methanol to provide the title compound. 1H NMR (300 MHz, DMSO-D6) δ ppm: 1.05-1.19 (m, 4 H), 2.22-2.41 (m, 1 H), 2.35 (s, 3 H), 7.05-7.31 (m, 7 H), 7.37 (s, 1 H), 7.58 (d, J=8.46 Hz, 1 H), 8.50 (s, 1 H), 8.65 (d, J=8.46 Hz, 1 H), 10.21 (s, 1 H); MS (ESI)+ m/z 385 (M+H)+.

Workup

  1. customto provide the crude residue which
  2. customwas purified by trituration with methanol

Sources & evidence

ORD record
ord-0e7ff9821b6c4fc58699c684b572c616
Source dataset
uspto-grants-2012_08
Patent number
US08236950B2

Reaction notes

Loading…