Aniline → HCID 22125054, compound

HRID 1858301Notes

Reaction equation

HRID 1858301 reaction equation
C(S([C:11]1[N:16]=[C:15]2[N:17]([CH2:29][CH:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)[C:18](=[O:28])[N:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[Br:27])[CH2:20][C:14]2=[CH:13][N:12]=1)(=O)=O)C1C=CC=CC=1.[NH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>>[NH:36]([C:11]1[N:16]=[C:15]2[N:17]([CH2:29][CH:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)[C:18](=[O:28])[N:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[Br:27])[CH2:20][C:14]2=[CH:13][N:12]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

3

Reactant 2

HCID 6115AnilineHCID 22125072HCID 22125072, compound

Product 1

HCID 22125054HCID 22125054, compoundYield 42%

Conditions

Temperature
150 °C

Procedure

A mixture of 240 mg (0.4 mmol) of 7-benzylsulfonyl-3-(2-bromophenyl)-1-cyclohexylmethyl-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one and 0.39 ml (4.3 mmol) of aniline was heated at 150° C. for 2 hours. The reaction mixture 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. The crude material was purified by flash chromatography on silica gel, eluting with 1:2 ethyl acetate/hexane. Product containing fractions were combined and evaporated to give 80 mg (42%) of 7-anilino-3-(2-bromophenyl)-1-cyclohexylmethyl-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one as an off-white solid of melting point 200-202° C. [Mass spectrum (ESI) MH+ =492].

Workup

  1. temperatureThe reaction mixture 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
  8. customThe crude material was purified by flash chromatography on silica gel
  9. washeluting with 1:2 ethyl acetate/hexane
  10. additionProduct containing fractions
  11. customevaporated

Sources & evidence

ORD record
ord-54473fd8fce7459d9d81600791c1cf9b
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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