Aniline → HCID 22125147, compound

HRID 1858229Notes

Reaction equation

HRID 1858229 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[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]=[CH:25][CH:24]=2)[C:10]1=[O:29].[NH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>>[NH:30]([C:14]1[N:13]=[C:12]2[N:11]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:10](=[O:29])[N:9]([C:3]3[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=3[Cl:8])[CH2:18][C:17]2=[CH:16][N:15]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

3

Reactant 2

HCID 6115AnilineHCID 22125142HCID 22125142, compound

Product 1

HCID 22125147HCID 22125147, compoundYield 11.3%

Conditions

Temperature
180 °C

Procedure

A mixture of 40 mg (0.096 mmol) of 3-(2,6-dichlorophenyl)-7-methanesulfonyl-3,4-dihydro-1-phenylpyrimido[4,5-d]pyrimidin-2(1H)-one and 1 ml (11 mmol) of aniline was heated at 180° C. for 45 minutes, cooled and partitioned between 30 ml of ethyl acetate and 30 ml of 2M hydrochloric acid. The separated organic phase was dried over magnesium sulfate, filtered and evaporated. The residue was subjected to column chromatography on silica gel using ethyl acetate/hexane (1:2) for the elution. Product-containing fractions were combined and evaporated to give a tan solid which was purified further by HPLC. The mobile phase was water/0.1% trifluoroacetic acid (A) and acetonitrile/0.07% trifluoroacetic acid (B); the gradient was 5%-95% B over 20 minutes; and the product was detected with an ultraviolet detector at a wavelength of 215 nm. The product-containing fraction was lyophilized to give 5 mg (4%) of 7-anilino-3-(2,6-dichlorophenyl)-3,4-dihydro-1-phenylpyrimido[4,5-d]pyrimidin-2(1H)-one as a white solid of melting point 138° C.

Workup

  1. temperaturecooled
  2. custompartitioned between 30 ml of ethyl acetate and 30 ml of 2M hydrochloric acid
  3. dry with materialThe separated organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. washfor the elution
  7. customevaporated
  8. customto give a tan solid which
  9. customwas purified further by HPLC
  10. customover 20 minutes

Sources & evidence

ORD record
ord-f8bc5c1c1bb94478a424a261189d8f8d
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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