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 1887189Notes

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]

Participants

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

temperatureThen the reaction is cooled to room temperature
customa pale yellow solid is formed
customThe solid is collected
washrinsed with water
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

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