{4-[2-(Diethylamino)ethoxy]phenyl}methanamine → HCID 22125117, compound

HRID 1858218Notes

Reaction equation

HRID 1858218 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]([CH3:23])[C:10]1=[O:24].[CH2:25]([N:27]([CH2:39][CH3:40])[CH2:28][CH2:29][O:30][C:31]1[CH:38]=[CH:37][C:34]([CH2:35][NH2:36])=[CH:33][CH:32]=1)[CH3:26]>>[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:36][CH2:35][C:34]3[CH:33]=[CH:32][C:31]([O:30][CH2:29][CH2:28][N:27]([CH2:39][CH3:40])[CH2:25][CH3:26])=[CH:38][CH:37]=3)=[N:15][CH:16]=2)[N:11]([CH3:23])[C:10]1=[O:24]

Participants

3

Reactant 2

HCID 235944{4-[2-(Diethylamino)ethoxy]phenyl}methanamineHCID 184254443-(2,6-dichlorophenyl)-7-methanesulfonyl-1-methyl-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one

Product 1

HCID 22125117HCID 22125117, compoundYield 29.1%

Conditions

Temperature
170 °C

Procedure

A mixture of 100 mg (0.26 mmol) of 3-(2,6-dichlorophenyl)-3,4-dihydro-7-methanesulfonyl-1-methylpyrimido[4,5-d]pyrimidin-2(1H)-one and 238 mg (1.07 mmol) of 4-(2-diethylaminoethoxy)benzylamine was heated at 170° C. for 30 minutes. The product was purified by flash column chromatography using dichloromethane/methanol/water/acetic acid (120:14:3:2) for the elution. Product-containing fractions were combined and evaporated to give 40 mg (29%) of 3-(2,6-dichlorophenyl)-7-[4-[2-(diethylamino)ethoxy]benzylamino]-3,4-dihydro-1-methylpyrimido[4,5-d]pyrimidin-2(1H)-one as a white solid of melting point 137-138° C.

Workup

  1. customThe product was purified by flash column chromatography
  2. washfor the elution
  3. customevaporated

Sources & evidence

ORD record
ord-c73134f7189d49b7af9d196d489e8769
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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