Ethanolamine → HCID 11826662, compound

HRID 378913Notes

Reaction equation

HRID 378913 reaction equation
Cl[C:2]1[N:3]=[C:4]([NH:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:5]2[N:10]=[C:9](Cl)[N:8]=[C:7]([NH:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:6]=2[N:20]=1.[CH2:29]([CH2:31][NH2:32])[OH:30]>O>[OH:30][CH2:29][CH2:31][NH:32][C:2]1[N:3]=[C:4]([NH:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:5]2[N:10]=[C:9]([NH:32][CH2:31][CH2:29][OH:30])[N:8]=[C:7]([NH:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:6]=2[N:20]=1

Participants

4

Reactant 2

HCID 700EthanolamineHCID 10873303HCID 10873303, compound

Product 1

HCID 11826662HCID 11826662, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 2,6-dichloro-4,8-di-(benzylamino)pyrimidopyrimidine (0.32 g, 0.78 mmol) and ethanolamine (2 ml) was stirred at 150° C. for 12 h. The reaction mixture was cooled to room temperature and water (15 ml) was added, after which the mixture was stirred for a further 20 min, filtered, washed with water, and the collected solid dried in vacuo. Purification by silica column chromatography (dichloromethane: methanol, 9:1) yielded the title compound (0.11 g, 31%) as a fluorescent yellow solid (Found: C, 61.0; H, 6.0; N, 23.7. C24H28N8O2.0.14CH2Cl2 requires C, 61.4; H, 5.6; N, 23.2); NMR data was as follows:

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringafter which the mixture was stirred for a further 20 min
  3. filtrationfiltered
  4. washwashed with water
  5. customthe collected solid dried in vacuo
  6. customPurification by silica column chromatography (dichloromethane: methanol, 9:1)

Sources & evidence

ORD record
ord-48e7f5277ce14a84a09b93d6ee8f2f75
Source dataset
uspto-grants-2001_10
Patent number
US06297250B1

Reaction notes

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