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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
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HRID 1887189 반응식
[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]
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참가 물질

6

반응물 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

생성물 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 ester수율 95%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4cdd4b190b4448edba623abdff0c72e8
출처 데이터셋
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08501749B2

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