Methylamine → HCID 22125000, compound

HRID 1858300Notes

Reaction equation

HRID 1858300 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.[CH3:40][NH2:41]>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][NH:41][CH3:40])[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

Participants

4

Reactant 2

HCID 6329MethylamineHCID 22125008HCID 22125008, compound

Product 1

HCID 22125000HCID 22125000, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 120 mg (0.2 mmol) of 7-anilino-3-(2,4-dichlorophenyl)-3,4-dihydro-1-[3-(2-methanesulfonyloxyethyl)phenyl]pyrimido[4,5-d]pyrimidin-2(1H)-one in 4 ml of 40% methylamine in ethanol was heated at 50° C. for 3 hours. The reaction mixture was evaporated and the crude material purified by flash column chromatography on silica gel eluting with dichloromethane/methanol/acetic acid/water (120:14:3:2). Product containing fractions were combined and evaporated to give 18 mg (16%) of 7-anilino-3-(2,4-dichlorophenyl)-3,4-dihydro-1-[3-[2-(methylamino)ethyl]phenyl]pyrimido[4,5-d]pyrimidin-2(1H)-one as a solid of melting point 120-122° C. [Mass spectrum (ESI) MH+ =519].

Workup

  1. customThe reaction mixture was evaporated
  2. customthe crude material purified by flash column chromatography on silica gel eluting with dichloromethane/methanol/acetic acid/water (120:14:3:2)
  3. additionProduct containing fractions
  4. customevaporated

Sources & evidence

ORD record
ord-50c4b82f9243419f875cf6e5ae317ee1
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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