Hydrochloric Acid → 2-[6-oxopyrimidin-1(6H)-yl]propanoic acid

HRID 1888176

반응식

HRID 1888176 반응식
[N:1]1[CH:6]=[CH:5][C:4](=[O:7])[NH:3][CH:2]=1.[OH-].[Na+].Br[C@H:11]([CH3:15])[C:12]([OH:14])=[O:13].Cl>>[O:7]=[C:4]1[N:3]([CH:11]([CH3:15])[C:12]([OH:14])=[O:13])[CH:2]=[N:1][CH:6]=[CH:5]1

참가 물질

5

반응물 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 206954-HydroxypyrimidineHCID 6992152(2R)-2-Bromopropanoic acid

생성물 1

HCID 579074812-[6-oxopyrimidin-1(6H)-yl]propanoic acid

반응 조건

온도
85 °C

실험 절차

To pyrimidin-4(3H)-one (0.908 g, 9.45 mmol) was added a 5 N sodium hydroxide solution (3.8 ml) followed by (2R)-2-bromopropanoic acid (0.95 ml, 11 mmol). The reaction mixture was heated at 85° C. for 1 h. After cooling to ambient temperature the reaction was neutralized with 2 N hydrochloric acid (5.2 ml) and then directly purified by reverse phase HPLC (TMC Pro-Pac C18; 0-40% 0.1% trifluoroacetic acid in aeetonitrile/0.1% trifluoroacetic acid in water gradient). Removal of the volatiles in vacuo afforded the title compound as a white solid. 1H NMR (DMSO-d6) δ: 8.48 (d, J=2.7 Hz, 1H), 7.88 (dd, J=7.8, 2.8 Hz, 1H), 6.12 (d, J=7.6 Hz, 1H), 5.04 (q, J=7.3 Hz, 1H), 1.64 (d, J=7.5 Hz, 3H). LC/MS 169.1 (M+1)+.

후처리

  1. temperatureAfter cooling to ambient temperature the reaction
  2. customdirectly purified by reverse phase HPLC (TMC Pro-Pac C18; 0-40% 0.1% trifluoroacetic acid in aeetonitrile/0.1% trifluoroacetic acid in water gradient)
  3. customRemoval of the volatiles in vacuo

출처 및 근거

ORD 기록
ord-58ac3fba3b4d4e06ad01a47d7df8aa23
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08501786B2

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