N'-(6-tert-Butyl-3-cyano-pyridin-2-yl)-N,N-dimethyl-formamidine → 4-[4-Benzyloxy-2-(7-tert-butyl-pyrido[2,3-d]pyrimidin-4-ylamino)-phenylsulfanyl]-phenol

HRID 607331Notes

Reaction equation

HRID 607331 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[CH:4][C:3]=1[S:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1.[C:24]([C:28]1[N:33]=[C:32]([N:34]=[CH:35]N(C)C)[C:31]([C:39]#[N:40])=[CH:30][CH:29]=1)([CH3:27])([CH3:26])[CH3:25]>C(O)(=O)C>[CH2:9]([O:8][C:6]1[CH:5]=[CH:4][C:3]([S:16][C:17]2[CH:18]=[CH:19][C:20]([OH:23])=[CH:21][CH:22]=2)=[C:2]([NH:1][C:39]2[C:31]3[CH:30]=[CH:29][C:28]([C:24]([CH3:25])([CH3:26])[CH3:27])=[N:33][C:32]=3[N:34]=[CH:35][N:40]=2)[CH:7]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 66808575N'-(6-tert-Butyl-3-cyano-pyridin-2-yl)-N,N-dimethyl-formamidineHCID 668085974-(2-Amino-4-benzyloxy-phenylsulfanyl)-phenol

Product 1

HCID 668085464-[4-Benzyloxy-2-(7-tert-butyl-pyrido[2,3-d]pyrimidin-4-ylamino)-phenylsulfanyl]-phenol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The product from Example 27A was heated at 130° C. in acetic acid with the product from Example 127A for 15 minutes, the mixture was then cooled to room temperature, the solvent removed and the residue purified by column chromatography on silica gel to provide the title product. 1H NMR (300 MHz, DMSO-D6) δ ppm: 1.38 (s, 9H) 5.11 (s, 2H) 6.60-6.74 (m, 2H) 6.94 (d, J=7.35 Hz, 1H) 7.06-7.19 (m, 3H) 7.27-7.50 (m, 6H) 7.78 (d, J=8.09 Hz, 1H) 8.56 (s, 1H) 8.75 (s, 1H) 9.64 (s, 1H) 9.95 (s, 1H); MS (ESI+) m/z 509 (M+H)+.

Workup

  1. customthe solvent removed
  2. customthe residue purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-cefbf68ef7f44caea16d7c917fd786c1
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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