Diethylamine → HCID 54210792, compound

HRID 1858337Notes

Reaction equation

HRID 1858337 reaction equation
[NH:1]([C:8]1[N:13]=[C:12]2[N:14]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([CH2:33][CH2:34]OS(C)(=O)=O)[CH:28]=3)[C:15](=[O:26])[N:16]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=3[Cl:25])[CH2:17][C:11]2=[CH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:40]([NH:42][CH2:43][CH3:44])[CH3:41]>C(O)C>[NH:1]([C:8]1[N:13]=[C:12]2[N:14]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([CH2:33][CH2:34][N:42]([CH2:43][CH3:44])[CH2:40][CH3:41])[CH:28]=3)[C:15](=[O:26])[N:16]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=3[Cl:25])[CH2:17][C:11]2=[CH:10][N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 22125008HCID 22125008, compound

Product 1

HCID 54210792HCID 54210792, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 58 mg (0.1 mmol) of 7-anilino-3-(2,4-dichlorophenyl)-3,4-dihydro-1-[3-(2-methanesulfonyloxyethyl)phenyl]-pyrimido[4,5-d]pyrimidin-2(1H)-one (prepared in Example 74) and 0.5 ml of diethylamine in 2 ml of ethanol was heated at 50° C. for 3 hours. The reaction mixture was evaporated and the crude material purified by flash chromatography on silica gel, eluting with 5% methanol in dichloromethane. Product containing fractions were combined and evaporated to give 16 mg (28%) of 7-anilino-3-(2,4-dichlorophenyl)-1-[3-[2-(diethylamino) ethyl]phenyl]-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one as an off-white solid of melting point 186° C. [Mass spectrum (ESI) MH+ =561].

Workup

  1. customThe reaction mixture was evaporated
  2. customthe crude material purified by flash chromatography on silica gel
  3. washeluting with 5% methanol in dichloromethane
  4. additionProduct containing fractions
  5. customevaporated

Sources & evidence

ORD record
ord-cc585e36dd574486a3e45fa0ef1acaf4
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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