Aniline → HCID 22125037, compound

HRID 1858289Notes

Reaction equation

HRID 1858289 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[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=[CH:24][CH:23]=2)[C:9]1=[O:32].[NH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>>[NH:33]([C:13]1[N:12]=[C:11]2[N:10]([C:22]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH:25]=[CH:24][CH:23]=3)[C:9](=[O:32])[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:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

3

Reactant 2

HCID 6115AnilineHCID 22124977HCID 22124977, compound

Product 1

HCID 22125037HCID 22125037, compoundYield 67%

Conditions

Temperature
120 °C

Procedure

A mixture of 160 mg (0.3 mmol) of 3-(2-bromophenyl)-3,4-dihydro-7-methanesulfonyl-1-(1-naphthyl)pyrimido[4,5-d]pyrimidin-2(1H)-one and 200 μl (2.2 mmol) of aniline was heated at 120° C. for 2 hours. The residue was partitioned between ethyl acetate (10 ml) and 2M hydrochloric acid (10 ml) and the ethyl acetate layer separated then washed with saturated aqueous sodium bicarbonate (10 ml), dried over magnesium sulfate, filtered and evaporated to give 100 mg (67%) of 7-anilino-3-(2-bromophenyl)-3,4-dihydro-1-(1-naphthyl)pyrimido[4,5-d]pyrimidin-2(1H)-one as an orange solid of melting point 120-125° C. [Mass spectrum (ESI) MH+ =522].

Workup

  1. customThe residue was partitioned between ethyl acetate (10 ml) and 2M hydrochloric acid (10 ml)
  2. customthe ethyl acetate layer separated
  3. washthen washed with saturated aqueous sodium bicarbonate (10 ml)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-f1543f38c79f4777b1f25d5b26fae83b
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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