HCID 18186500, compound → HCID 18186458, compound

HRID 1357520Notes

Reaction equation

HRID 1357520 reaction equation
Cl.Cl.[NH:3]([C:10]1[C:15]([CH2:16][O:17]CC)=[CH:14][N:13]=[C:12]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH:29]([OH:34])[CH2:30][N:31]([CH3:33])[CH3:32])=[CH:23][CH:22]=2)[N:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>O>[NH:3]([C:10]1[C:15]([CH2:16][OH:17])=[CH:14][N:13]=[C:12]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH:29]([OH:34])[CH2:30][N:31]([CH3:32])[CH3:33])=[CH:23][CH:22]=2)[N:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

3

Reactant 1

HCID 18186500HCID 18186500, compound

Product 1

HCID 18186458HCID 18186458, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Anilino-5-(ethoxymethyl)-2-{4-[2-hydroxy-3-(N,N-dimethylamino)propoxy]anilino}pyrimidine dihydrochloride (Example 86; 50 mg, 0.11 mmol) was dissolved in water (3 ml) and the solution was heated under reflux for 3 hours. Volatile material was removed by evaporation and the residue was triturated with diethyl ether, giving the product as a hygroscopic dihydrochloride salt (35 mg, 75%). NMR: 2.81 (dd, 2H), 3.1-3.3 (m, 2H), 3.94 (m, 2H), 4.28 (m, 1H), 4.38 (d, 1H), 4.51 (s, 2H), 6.88 (d, 2H), 7.22 (t, 1H), 7.32 (d, 2H), 7.37 (dd, 2H), 7.56 (d, 2H), 7.93 (s, 1H), 9.91 (s, 1H) 9.91 (br s, 1H), 10.55 (s, 1H); MS (MH+): 410.3.

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 3 hours
  3. customVolatile material was removed by evaporation
  4. customthe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-9155807e12884f099f8ff220d629d768
Source dataset
uspto-grants-2003_07
Patent number
US06593326B1

Reaction notes

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