1-Naphthylamine → HCID 22125128, compound

HRID 1858216Notes

Reaction equation

HRID 1858216 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[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=[CH:33][CH:32]=1>>[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]([NH:30][C:31]3[C:40]4[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=4)[CH:34]=[CH:33][CH:32]=3)=[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]

Participants

3

Reactant 2

HCID 86401-NaphthylamineHCID 22125142HCID 22125142, compound

Product 1

HCID 22125128HCID 22125128, compoundYield 40.8%

Conditions

Temperature
130 °C

Procedure

A mixture of 100 mg (0.22 mmol) of 3-(2,6-dichlorophenyl)-7-methanesulfonyl-1-phenyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one and 320 mg (2.2 mmol) of 1-aminonaphthalene was heated at 130° C. for 4 hours. The mixture was left to cool and was then partitioned between 10 ml of ethyl acetate and 2M hydrochloric acid. The insoluble 1-aminonaphthalene hydrochloride was removed by filtration. The ethyl acetate phase was separated, washed with 10 ml of saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography on silica gel using ethyl acetate/hexane (1:1) for the elution. Product-containing fractions were evaporated to give 46 mg (40%) of 3-(2,6-dichlorophenyl)-3,4-dihydro-7-(1-naphthylamino)-1-phenylpyrimido[4,5-d]pyrimidin-2(1H)-one as a pale pink solid of melting point 213-214° C.

Workup

  1. waitThe mixture was left
  2. temperatureto cool
  3. customwas then partitioned between 10 ml of ethyl acetate and 2M hydrochloric acid
  4. customThe insoluble 1-aminonaphthalene hydrochloride was removed by filtration
  5. customThe ethyl acetate phase was separated
  6. washwashed with 10 ml of saturated aqueous sodium bicarbonate solution
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified by flash column chromatography on silica gel
  11. washfor the elution
  12. customProduct-containing fractions were evaporated

Sources & evidence

ORD record
ord-7565c4f140d242f196e038b4fa6ce89d
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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