Aniline → HCID 22124975, compound

HRID 1858305Notes

Reaction equation

HRID 1858305 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][C:26]([CH2:29][OH:30])=[CH:25][CH:24]=2)[C:10]1=[O:31].[NH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>>[NH:32]([C:14]1[N:13]=[C:12]2[N:11]([C:23]3[CH:28]=[CH:27][C:26]([CH2:29][OH:30])=[CH:25][CH:24]=3)[C:10](=[O:31])[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:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

3

Reactant 2

HCID 6115AnilineHCID 22125030HCID 22125030, compound

Product 1

HCID 22124975HCID 22124975, compoundYield 57%

Conditions

Temperature
120 °C

Procedure

A mixture of 350 mg (0.7 mmol) of 3-(2,4-dichlorophenyl)-3,4-dihydro-1-[4-(hydroxymethyl)phenyl]-7-methanesulfonyl-pyrimido[4,5-d]pyrimidin-2(1H)-one and 2 ml of aniline was heated at 120° C. for 3 hours. The reaction was cooled to room temperature then partitioned between 2M hydrochloric acid (20 ml) and dichloromethane (20 ml). The organic layer was separated, washed with saturated aqueous sodium bicarbonate (20 ml), dried over magnesium sulfate, filtered and evaporated to give 200 mg (57%) of 7-anilino-3-(2,4-dichlorophenyl)-3,4-dihydro-1-[4-(hydroxymethyl)phenyl]pyrimido[4,5-d]pyrimidin-2(1H)-one as a yellow solid of melting point 121-125° C. [Mass spectrum (ESI) MH+ =492].

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customthen partitioned between 2M hydrochloric acid (20 ml) and dichloromethane (20 ml)
  3. customThe organic layer was separated
  4. washwashed with saturated aqueous sodium bicarbonate (20 ml)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-f45011ef37a7440db0dda60167104d61
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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