Aniline → HCID 22125121, compound

HRID 1858297Notes

Reaction equation

HRID 1858297 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[CH2:18][C:17]2[C:12](=[N:13][C:14](S(C)(=O)=O)=[N:15][CH:16]=2)[N:11]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][CH2:30][OH:31])[CH:24]=2)[C:10]1=[O:32].[NH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>>[NH:33]([C:14]1[N:13]=[C:12]2[N:11]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][CH2:30][OH:31])[CH:24]=3)[C:10](=[O:32])[N:9]([C:3]3[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=3[Cl:1])[CH2:18][C:17]2=[CH:16][N:15]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

3

Reactant 2

HCID 6115AnilineHCID 22124980HCID 22124980, compound

Product 1

HCID 22125121HCID 22125121, compoundYield 55%

Conditions

Temperature
120 °C

Procedure

A mixture of 1.09 g (2.2 mmol) of 3-(2,4-dichlorophenyl)-3,4-dihydro-1-[3-(2-hydroxyethyl)phenyl]-7-methanesulfonyl-pyrimido[4,5-d]pyrimidin-2(1H)-one and aniline was heated at 120° C. for 1 hour. The reaction mixture was partitioned between dichloromethane (20 ml) and 2M hydrochloric acid (20 ml) and the dichloromethane layer separated, washed with saturated aqueous sodium bicarbonate (20 ml), dried over magnesium sulfate, filtered and evaporated. The crude material was purified by flash chromatography on silica gel, eluting with 5:1 ethyl acetate/hexane. Product containing fractions were combined and evaporated to give 630 mg (55%) of 7-anilino-3-(2,4-dichlorophenyl)-3,4-dihydro-1-[3-(2-hydroxyethyl)phenyl]pyrimido[4,5-d]pyrimidin-2(1H)-one as a white solid of melting point 213-217° C. [Mass spectrum (ESI) MH+ =506].

Workup

  1. customThe reaction mixture was partitioned between dichloromethane (20 ml) and 2M hydrochloric acid (20 ml)
  2. customthe dichloromethane layer separated
  3. washwashed with saturated aqueous sodium bicarbonate (20 ml)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude material was purified by flash chromatography on silica gel
  8. washeluting with 5:1 ethyl acetate/hexane
  9. additionProduct containing fractions
  10. customevaporated

Sources & evidence

ORD record
ord-875cf42288eb4434ac2c116baf6679ea
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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