p-Aminophenylacetic acid ethyl ester → HCID 22125060, compound

HRID 1858208Notes

Reaction equation

HRID 1858208 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].[NH2:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:28][CH:27]=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:25][C:26]3[CH:27]=[CH:28][C:29]([CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:30][CH:31]=3)=[N:15][CH:16]=2)[N:11]([CH3:23])[C:10]1=[O:24]

Participants

3

Reactant 2

HCID 225219p-Aminophenylacetic acid ethyl esterHCID 184254443-(2,6-dichlorophenyl)-7-methanesulfonyl-1-methyl-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one

Product 1

HCID 22125060HCID 22125060, compoundYield 38%

Conditions

Temperature
185 °C

Procedure

A mixture of 200 mg (0.52 mmol) of 3-(2,6-dichlorophenyl)-3,4-dihydro-7-methanesulfonyl-1-methylpyrimido[4,5-d]pyrimidin-2(1H)-one and 800 mg (4.47 mmol) of ethyl 4-aminophenylacetate was heated at 185° C. for 45 minutes. The residue was partitioned between 10 ml of ethyl acetate and 10 ml of 2M hydrochloric acid and the insoluble cream colored solid was collected by filtration and washed with 20 ml of water and 20 ml of ethyl acetate and then dried under a high vacuum. 95 mg (38%) of ethyl 2-[4-[[3-(2,6-dichlorophenyl)-1,2,3,4-tetrahydro-1-methyl-2-oxopyrimido[4,5-d]pyrimidin-7-yl]amino]phenyl]acetate of melting point 211-212° C. were isolated.

Workup

  1. customThe residue was partitioned between 10 ml of ethyl acetate and 10 ml of 2M hydrochloric acid
  2. filtrationthe insoluble cream colored solid was collected by filtration
  3. washwashed with 20 ml of water and 20 ml of ethyl acetate
  4. customdried under a high vacuum

Sources & evidence

ORD record
ord-adb53c97ee8149069711ffc3c25fb204
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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