HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Water → [1-(1,4-dimethyl-1H-indol-3-ylmethyl)-2,4-dioxo-1,4-dihydro-2H-pyrido[3,4-d]pyrimidin-3-yl]-acetic acid methyl ester

HRID 1887189
Notes
Print preview

Reaction equation

HRID 1887189 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH2:4][N:5]1[C:10](=[O:11])[C:9]2[CH:12]=[CH:13][N:14]=[CH:15][C:8]=2[NH:7][C:6]1=[O:16].[I-].[CH3:19][N:20]1[C:28]2[C:23](=[C:24]([CH3:29])[CH:25]=[CH:26][CH:27]=2)[C:22]([CH2:30][N+](C)(C)C)=[CH:21]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:1][O:2][C:3](=[O:17])[CH2:4][N:5]1[C:10](=[O:11])[C:9]2[CH:12]=[CH:13][N:14]=[CH:15][C:8]=2[N:7]([CH2:30][C:22]2[C:23]3[C:28](=[CH:27][CH:26]=[CH:25][C:24]=3[CH3:29])[N:20]([CH3:19])[CH:21]=2)[C:6]1=[O:16]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 17836486((1,4-Dimethylindole-3-yl)methyl)trimethylammonium iodideHCID 67502666(2,4-dioxo-1,4-dihydro-2H-pyrido[3,4-d]pyrimidin-3-yl)-acetic acid methyl ester

Product 1

HCID 67502958[1-(1,4-dimethyl-1H-indol-3-ylmethyl)-2,4-dioxo-1,4-dihydro-2H-pyrido[3,4-d]pyrimidin-3-yl]-acetic acid methyl ester
Yield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 62 mg of (2,4-dioxo-1,4-dihydro-2H-pyrido[3,4-d]pyrimidin-3-yl)-acetic acid methyl ester in N,N-dimethylformamide (2.5 mL) is added 109 mg of (1,4-dimethyl-1H-indol-3-ylmethyl)-trimethylammonium iodide and 44 mg of potassium carbonate at room temperature. The solution is heated to 60° C. for 2.5 h. Then the reaction is cooled to room temperature and stirred for another 16 hrs. Then 50 mL of water is added and a pale yellow solid is formed. The solid is collected and rinsed with water. Purification of this solid by flash chromatography on silica gel gives 98 mg (95%) of [1-(1,4-dimethyl-1H-indol-3-ylmethyl)-2,4-dioxo-1,4-dihydro-2H-pyrido[3,4-d]pyrimidin-3-yl]-acetic acid methyl ester.

Workup

  1. temperatureThen the reaction is cooled to room temperature
  2. customa pale yellow solid is formed
  3. customThe solid is collected
  4. washrinsed with water
  5. customPurification of this solid by flash chromatography on silica gel

Sources & evidence

ORD record
ord-4cdd4b190b4448edba623abdff0c72e8
Source dataset
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08501749B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes