Hydrochloric Acid → (R)-1-[4-(2-Methyl-4-phenyl-5,8-dihydro-6H-pyrido[3,4-d]pyrimidin-7-yl)-pyrimidin-2-yl]ethanol

HRID 586172노트

반응식

HRID 586172 반응식
C([O:6][C@@H:7]([C:9]1[N:14]=[C:13]([N:15]2[CH2:24][CH2:23][C:22]3[C:21]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[N:20][C:19]([CH3:31])=[N:18][C:17]=3[CH2:16]2)[CH:12]=[CH:11][N:10]=1)[CH3:8])(=O)CCC.Cl.[OH-].[Na+]>O1CCOCC1>[CH3:31][C:19]1[N:20]=[C:21]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:22]2[CH2:23][CH2:24][N:15]([C:13]3[CH:12]=[CH:11][N:10]=[C:9]([C@H:7]([OH:6])[CH3:8])[N:14]=3)[CH2:16][C:17]=2[N:18]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 53875213(R)-1-[4-(2-methyl-4-phenyl-5,8-dihydro-6H-pyrido[3,4-d]pyrimidin-7-yl)-pyrimidin-2-yl]-ethyl butyrate

생성물 1

HCID 20767624(R)-1-[4-(2-Methyl-4-phenyl-5,8-dihydro-6H-pyrido[3,4-d]pyrimidin-7-yl)-pyrimidin-2-yl]ethanol수율 88%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

To a solution of (R)-1-[4-(2-methyl-4-phenyl-5,8-dihydro-6H-pyrido[3,4-d]pyrimidin-7-yl)-pyrimidin-2-yl]-ethyl butyrate (prepared according to the method of Example 86, Step E, 11.0 g, 26.4 mmol) in dioxane (13 mL) was added concentrated hydrochloric acid (22 mL, 264 mmol). This mixture was stirred at room temperature overnight, cooled to 0° C., neutralized via slow addition of 6 N aqueous sodium hydroxide, and extracted with ethyl acetate (4×). The combined organic extracts were dried over sodium sulfate, filtered, evaporated, and purified by flash column chromatography (2→5% methanol/ethyl acetate) to give an oil which after titration with hexanes provided 8.0 g (88%) of the title compound as a white solid. mp: 114-116° C.; 1H NMR (CD3OD, 250 MHz) δ 8.26 (d, 1H), 7.62-7.47 (c, 5H), 6.52 (d, 1H), 4.79 (s, 2H), 4.66 (q, 1H), 4.24 (br s, 1H), 3.90-3.80 (c, 2H), 2.95 (t, 2H), 2.70 (s, 3H), 1.49 (d, 3H); MS (APCI) 348 (MH+), [α]D+15.6 (c 1.0, MeOH).

후처리

  1. extractionextracted with ethyl acetate (4×)
  2. dry with materialThe combined organic extracts were dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. custompurified by flash column chromatography (2→5% methanol/ethyl acetate)
  6. customto give an oil which after titration with hexanes

출처 및 근거

ORD 기록
ord-2f5172bcdfe14b93bdbbcec9261012be
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06936600B2

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