1-(4-Aminophenoxy)-3-ethoxypropan-2-ol → 4-Anilino-5-bromo-2-{4-[3-ethoxy-2-(hydroxy)propoxy]anilino}pyrimidine

HRID 1357534Notes

Reaction equation

HRID 1357534 reaction equation
[NH:1]([C:8]1[C:13]([Br:14])=[CH:12][N:11]=[C:10](Cl)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:16]([O:18][CH2:19][CH:20]([OH:30])[CH2:21][O:22][C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=1)[CH3:17]>>[NH:1]([C:8]1[C:13]([Br:14])=[CH:12][N:11]=[C:10]([NH:27][C:26]2[CH:28]=[CH:29][C:23]([O:22][CH2:21][CH:20]([OH:30])[CH2:19][O:18][CH2:16][CH3:17])=[CH:24][CH:25]=2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 107748571-(4-Aminophenoxy)-3-ethoxypropan-2-olHCID 114033895-bromo-2-chloro-N-phenylpyrimidin-4-amine

Product 1

HCID 181864944-Anilino-5-bromo-2-{4-[3-ethoxy-2-(hydroxy)propoxy]anilino}pyrimidineYield 21%

Procedure

Using an analogous method to that described in Example 136, but starting from 4-anilino-5-bromo-2-chloropyrimidine (Method 13) and 4-[3-ethoxy-2-(hydroxy)propoxy]aniline (obtained as described in J. Med. Chem., 1998, 41, 330-36), the product was obtained in 21% yield. NMR: 1.10 (t, 3H), 3.42 (m, 2H), 3.45 (q, 2H), 3.75-3.9 (m, 3H), 4.99 (d, 1H), 6.74 (d, 2H), 7.12 (t, 1H), 7.33 (dd, 2H), 7.44 (d, 2H), 7.60 (d, 2H), 8.15 (s, 1H), 9.10 (s, 1H); MS (MH+): 459.3, 461.4.

Workup

  1. customthe product was obtained in 21% yield

Sources & evidence

ORD record
ord-70e2cc2cd5424bceaf2a0efc8a2988aa
Source dataset
uspto-grants-2003_07
Patent number
US06593326B1

Reaction notes

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