4-(2-Amino-4-methyl-phenylsulfanyl)-phenol → 4-[4-(3-Bromo-benzyloxy)-2-(pyrimido[4,5-d]pyrimidin-4-ylamino)-phenylsulfanyl]-phenol

HRID 607279Notes

Reaction equation

HRID 607279 reaction equation
[C:1]([C:3]1[C:4]([N:9]=[CH:10][N:11](C)C)=[N:5][CH:6]=[N:7][CH:8]=1)#[N:2].N[C:15]1[CH:20]=[C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([Br:29])[CH:24]=2)[CH:18]=[CH:17][C:16]=1[S:30][C:31]1[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=1.NC1C=C(C)C=CC=1SC1C=CC(O)=CC=1.C(C1C(N=CN(C)C)=NC(SCC)=NC=1)#N>>[Br:29][C:25]1[CH:24]=[C:23]([CH:28]=[CH:27][CH:26]=1)[CH2:22][O:21][C:19]1[CH:20]=[CH:15][C:16]([S:30][C:31]2[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=2)=[C:17]([NH:2][C:1]2[C:3]3[C:4](=[N:5][CH:6]=[N:7][CH:8]=3)[N:9]=[CH:10][N:11]=2)[CH:18]=1

Participants

5

Reactant 4

HCID 668081234-(2-Amino-4-methyl-phenylsulfanyl)-phenolHCID 668082684-[2-Amino-4-(3-bromo-benzyloxy)-phenylsulfanyl]-phenol2×HCID 66808339N'-(5-Cyano-pyrimidin-4-yl)-N,N-dimethyl-formamidine2×HCID 66808651N'-(5-Cyano-2-ethylsulfanyl-pyrimidin-4-yl)-N,N-dimethyl-formamidine

Product 1

HCID 602048124-[4-(3-Bromo-benzyloxy)-2-(pyrimido[4,5-d]pyrimidin-4-ylamino)-phenylsulfanyl]-phenol

Procedure

The product from Example 194A was reacted with the product from Example 15A according to the procedure from Example 156C substituting the product from Example 15A for the product from Example 6c and substituting the product from Example 194A for the product from Example 156B to provide the crude product which was purified by HPLC with NH4OAc to provide the title compound. 1H NMR (300 MHz, DMSO-D6) δ ppm: 5.12 (s, 2H), 6.64 (d, J=8.82 Hz, 2H), 6.93-7.04 (m, 1H), 7.10 (d, J=8.82 Hz, 2H), 7.14-7.23 (m, 2H), 7.36 (t, J=7.72 Hz, 1H), 7.43-7.49 (m, 1H), 7.54 (dt, J=7.81, 1.61 Hz, 1H), 7.65 (d, J=1.47 Hz, 1H), 9.04 (m, 1H), 9.63 (s, 1H), 10.29 (m, 1H); MS (ESI−) m/z 531 (M−H)−.

Workup

  1. customto provide the crude product which
  2. customwas purified by HPLC with NH4OAc

Sources & evidence

ORD record
ord-c1a1017425d64141a254674cb979c0fd
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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