4-(2-(Diethylamino)ethoxy)aniline → HCID 68859594, compound

HRID 1783560Notes

Reaction equation

HRID 1783560 reaction equation
[CH2:1]([N:4]1[C:13](=[O:14])[C:12]2[C:7](=[N:8][C:9]([N:15]3[CH:19]=[CH:18]N=C3)=[N:10][CH:11]=2)[N:6]([CH:20]([CH3:22])[CH3:21])[C:5]1=[O:23])[CH:2]=[CH2:3].[CH2:24]([N:26]([CH2:37][CH3:38])[CH2:27][CH2:28][O:29][C:30]1[CH:36]=CC(N)=[CH:32][CH:31]=1)[CH3:25]>C(Cl)(Cl)Cl>[CH2:1]([N:4]1[C:13](=[O:14])[C:12]2[C:7](=[N:8][C:9]([NH:15][C:19]3[CH:18]=[CH:36][C:30]([O:29][CH2:28][CH2:27][N:26]([CH2:37][CH3:38])[CH2:24][CH3:25])=[CH:31][CH:32]=3)=[N:10][CH:11]=2)[N:6]([CH:20]([CH3:22])[CH3:21])[C:5]1=[O:23])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 4189324-(2-(Diethylamino)ethoxy)anilineHCID 68859079HCID 68859079, compound

Product 1

HCID 68859594HCID 68859594, compoundYield 36.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 200 mg (0.64 mmol) of 3-allyl-7-(imidazol-1-yl)-1-isopropyl-1H-pyrimido[4,5-d]pyrimidine-2,4-dione and 400 mg (1.92 mmol) of 4-(2-diethylaminoethoxy)aniline is heated at 180° C. for 3 hours. The reaction mixture is cooled, dissolved into chloroform, and chromatographed on silica eluting with 4:96 methanol/chloroform. The resulting oily material partially crystallizes on standing, and the mixture is triturated with diethyl ether/hexane and filtered to give 106 mg (36%) of the title compound: mp 90-96° C.

Workup

  1. temperatureThe reaction mixture is cooled
  2. customchromatographed on silica eluting with 4:96 methanol/chloroform
  3. customThe resulting oily material partially crystallizes
  4. customthe mixture is triturated with diethyl ether/hexane
  5. filtrationfiltered

Sources & evidence

ORD record
ord-6f2ebe804dea4f879cae4969f796df40
Source dataset
uspto-grants-2009_03
Patent number
US07501425B1

Reaction notes

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