Aniline → HCID 22124973, compound

HRID 1858281Notes

Reaction equation

HRID 1858281 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:17][C:16]2[C:11](=[N:12][C:13](S(C)(=O)=O)=[N:14][CH:15]=2)[N:10]([C:22]2[CH:27]=[CH:26][C:25]([CH2:28][OH:29])=[CH:24][CH:23]=2)[C:9]1=[O:30].[NH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>>[NH:31]([C:13]1[N:12]=[C:11]2[N:10]([C:22]3[CH:27]=[CH:26][C:25]([CH2:28][OH:29])=[CH:24][CH:23]=3)[C:9](=[O:30])[N:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Br:1])[CH2:17][C:16]2=[CH:15][N:14]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

3

Reactant 2

HCID 6115AnilineHCID 22125013HCID 22125013, compound

Product 1

HCID 22124973HCID 22124973, compoundYield 35%

Conditions

Temperature
120 °C

Procedure

A mixture of 180 mg (0.37 mmol) of 3-(2-bromophenyl)-3,4-dihydro-1-[4-(hydroxymethyl)phenyl]-7-methanesulfonyl-pyrimido[4,5-d]pyrimidin-2(1H)-one and 0.34 ml (3.7 mmol) of aniline was heated at 120° C. for 3 hours. The reaction mixture was cooled to room temperature then triturated with 5 ml of 2M hydrochloric acid. The fawn solid was collected by filtration, washed with water then diethyl ether. The crude material was purified by flash chromatography on silica gel, using 3% methanol in dichloromethane for the elution. Product containing fractions were combined and evaporated to give 65 mg (35%) of 7-anilino-3-(2-bromophenyl)-3,4-dihydro-1-[4-(hydroxymethyl)phenyl]pyrimido[4,5-d]pyrimidin-2(1H)-one as an off-white solid of melting point 129-132° C. [Mass spectrum (ESI) MH+ =502].

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthen triturated with 5 ml of 2M hydrochloric acid
  3. filtrationThe fawn solid was collected by filtration
  4. washwashed with water
  5. customThe crude material was purified by flash chromatography on silica gel
  6. washfor the elution
  7. additionProduct containing fractions
  8. customevaporated

Sources & evidence

ORD record
ord-63f8114d144c4d4eadfdcfc8ff889d9c
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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