Potassium Carbonate → 5-(2,4-Dioxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidin-7-yl)-2-methoxybenzyl pivalate

HRID 218347노트

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HRID 218347 반응식
[NH2:1][C:2]1[NH:7][C:6](=[O:8])[NH:5][C:4](=[O:9])[CH:3]=1.[C:10]([O:16][CH2:17][C:18]1[CH:23]=[C:22]([C:24](=O)/[CH:25]=[CH:26]/N(C)C)[CH:21]=[CH:20][C:19]=1[O:31][CH3:32])(=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12].[OH-].[K+].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.O.C(O)(=O)C>[C:10]([O:16][CH2:17][C:18]1[CH:23]=[C:22]([C:24]2[CH:25]=[CH:26][C:3]3[C:4](=[O:9])[NH:5][C:6](=[O:8])[NH:7][C:2]=3[N:1]=2)[CH:21]=[CH:20][C:19]=1[O:31][CH3:32])(=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12]

참가 물질

8

반응물 4

HCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 701206-AminouracilHCID 580154715-[(2E)-3-(dimethylamino)prop-2-enoyl]-2-methoxybenzyl pivalate

생성물 1

HCID 445542295-(2,4-Dioxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidin-7-yl)-2-methoxybenzyl pivalate수율 91.7%

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 679Dimethyl Sulfoxide용매HCID 962Water용매2회

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온도
99 °C

실험 절차

6-Aminouracil (2.50 g, 19.1 mmol) was added to glacial acetic acid (24.6 mL) and water (6.1 mL) and the mixture heated to 99° C. A solution of 5-[(2E)-3-(dimethylamino)prop-2-enoyl]-2-methoxybenzyl pivalate (3.1 g, 9.5 mmol) in DMSO (9.2 mL) was then added over 280 minutes. The reaction was stirred at 99° C. for a further 50 minutes and cooled to 0° C. A solution of potassium hydroxide (24 g, 363.6 mmol) in water (48 mL) was then added to achieve a pH of around 7.0. Aqueous potassium carbonate was then added to afford a pH of around 10. After an hour at RT, a beige solid was filtered off, washed three times with aqueous potassium carbonate and pulled visibly dry on the filter. The beige solid was then added to a solution of citric acid (7.1 g) in water (44 ml) and the mixture maintained at 20° C. for 60 minutes. The resulting creamy white solid was isolated by filtration and washed with water until neutral pH of the wash liquors was obtained. The solid was dried to constant weight in vacuo thus affording 3.34 g of desired product (3).

후처리

  1. temperaturecooled to 0° C
  2. customto afford a pH of around 10
  3. waitAfter an hour at RT
  4. filtrationa beige solid was filtered off
  5. washwashed three times with aqueous potassium carbonate
  6. custompulled visibly dry on the filter
  7. additionThe beige solid was then added to a solution of citric acid (7.1 g) in water (44 ml)
  8. temperaturethe mixture maintained at 20° C. for 60 minutes
  9. customThe resulting creamy white solid was isolated by filtration
  10. washwashed with water until neutral pH of the wash liquors
  11. customwas obtained
  12. customThe solid was dried to constant weight in vacuo

출처 및 근거

ORD 기록
ord-35780bc51c1d4497b72efc4294016f08
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198441B2

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