Aniline → HCID 22125032, compound

HRID 1858236Notes

Reaction equation

HRID 1858236 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]=[C:25]([CH2:29][CH2:30][N:31]3[C:35](=[O:36])[C:34]4=[CH:37][CH:38]=[CH:39][CH:40]=[C:33]4[C:32]3=[O:41])[CH:24]=2)[C:10]1=[O:42].[NH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>>[NH:43]([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][N:31]4[C:32](=[O:41])[C:33]5=[CH:40][CH:39]=[CH:38][CH:37]=[C:34]5[C:35]4=[O:36])[CH:24]=3)[C:10](=[O:42])[N:9]([C:3]3[C:4]([Cl:8])=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[CH2:18][C:17]2=[CH:16][N:15]=1)[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Participants

3

Reactant 2

HCID 6115AnilineHCID 221250253-(2,6-dichlorophenyl)-7-methanesulfonyl-3,4-dihydro-1-[3-(2-phthalimidoethyl)phenyl]pyrimido[4,5-d]pyrimidin-2(1H)-one

Product 1

HCID 22125032HCID 22125032, compoundYield 29%

Conditions

Temperature
180 °C

Procedure

A mixture of 200 mg (0.52 mmol) of 3-(2,6-dichlorophenyl)-7-methanesulfonyl-3,4-dihydro-1-[3-(2-phthalimidoethyl)phenyl]pyrimido[4,5-d]pyrimidin-2(1H)-one and 3 ml of aniline was heated at 180° C. for 40 minutes and then cooled. The mixture was partitioned between 40 ml of dichloromethane and 40 ml of 2M hydrochloric acid. The organic phase was dried over magnesium sulfate, filtered and evaporated. The residue was subjected to column chromatography on silica gel using diethyl ether/hexane (1:1) for the elution. The product-containing fractions were combined and evaporated to give 30 mg (29%) of 7-anilino3-(2,6-dichlorophenyl)-3,4-dihydro-1-[3-(2-phthalimidoethyl)phenyl]pyrimido[4,5-d]pyrimidin-2(1H)-one as a white solid of melting point 142° C.

Workup

  1. temperaturecooled
  2. customThe mixture was partitioned between 40 ml of dichloromethane and 40 ml of 2M hydrochloric acid
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. washfor the elution
  7. customevaporated

Sources & evidence

ORD record
ord-d27f03c3492c4df0a94322df6c0828e3
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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