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Sodium Bicarbonate → 8-[(4-Bromophenyl)methyl]-4-methyl-2-methoxymethyl-5,8-dihydro-6H-pyrido[2,3-d]pyrimidin-7-one

HRID 129009
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HRID 129009 반응식
Cl[C:2]1[C:7]([CH2:8][CH2:9][C:10]([O:12]CC)=O)=[C:6]([CH3:15])[N:5]=[C:4]([CH2:16][O:17][CH3:18])[N:3]=1.Cl.[Br:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][NH2:26])=[CH:23][CH:22]=1.C([O-])(O)=O.[Na+]>C(O)CCC>[Br:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][N:26]2[C:2]3[N:3]=[C:4]([CH2:16][O:17][CH3:18])[N:5]=[C:6]([CH3:15])[C:7]=3[CH2:8][CH2:9][C:10]2=[O:12])=[CH:23][CH:22]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 27240964-Bromobenzylamine hydrochlorideHCID 19372999Ethyl 3-(4-Chloro-6-methyl-2-methoxymethylpyrimidin-5-yl)propionate

생성물 1

HCID 149168398-[(4-Bromophenyl)methyl]-4-methyl-2-methoxymethyl-5,8-dihydro-6H-pyrido[2,3-d]pyrimidin-7-one수율 73.6%

시약·촉매·용매 1

HCID 2631-Butanol용매

실험 절차

A mixture of ethyl 3-(4-chloro-6-methyl-2-methoxymethylpyrimidin-5-yl)propionate (3.6 g, 0.013 mol), 4-bromobenzylamine hydrochloride (3.0 g, 0.013 mol), NaHCO3 (2.4 g, 0.028 mol), and nBuOH (25 mL) was heated under reflux for 24 h. The mixture was concentrated, taken up in water, and extracted with CH2Cl2. The combined extracts were dried (MgSO4) and concentrated to give a brown oil. Purification by flash chromatography (5% MeOH/CH2Cl2) gave 3.6 g (72%) of product as an off-white solid, mp 64°-66° C.

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 24 h
  3. concentrationThe mixture was concentrated
  4. extractionextracted with CH2Cl2
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. concentrationconcentrated
  7. customto give a brown oil
  8. customPurification by flash chromatography (5% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-83ecdc475cbd4350ac3d23162a740bd2
출처 데이터셋
uspto-grants-1995_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05466692

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