Dimethyl Carbonate → 6-bromo-1H,2H,4H-pyrido(2,3-d)(1,3)oxazin-2-one

HRID 225890노트

반응식

HRID 225890 반응식
[NH2:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][C:5]([Br:10])=[CH:4][N:3]=1.[C:11](=O)(OC)[O:12]C.C[O-].[Na+]>CO>[Br:10][C:5]1[CH:4]=[N:3][C:2]2[NH:1][C:11](=[O:12])[O:9][CH2:8][C:7]=2[CH:6]=1

참가 물질

5

반응물 3

HCID 12021Dimethyl CarbonateHCID 108913662-Amino-5-bromo-3-(hydroxymethyl)pyridineHCID 10942334Sodium Methoxide

생성물 1

HCID 159259906-bromo-1H,2H,4H-pyrido(2,3-d)(1,3)oxazin-2-one수율 51%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a stirred solution of 2-amino-5-bromo-3-(hydroxymethyl)pyridine (3.0 g, 15 mmole) in methanol (30 mL) was added dimethyl carbonate (5 mL, 60 mmole) and sodium methoxide (25 wt % solution in methanol, 4 mL, 17.4 mmole). The reaction was heated at reflux for 18 hr, cooled to RT, and concentrated to dryness. The remaining residue was triturated with saturated aqueous NH4Cl (50 mL), filtered, washed with cold H2O (50 mL), and dried under vacuum to give the tide compound (1.75 g, 51%) as a beige solid: LCMS (ES) m/e 229.0 (M+H)+; 1H NMR (400 MHz, DMSO-d6) δ 10.90 (s, 1 H), 8.31 (s, 1 H), 7.90 (s, 1 H), 5.31 (s, 2 H).

후처리

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 18 hr
  3. concentrationconcentrated to dryness
  4. customThe remaining residue was triturated with saturated aqueous NH4Cl (50 mL)
  5. filtrationfiltered
  6. washwashed with cold H2O (50 mL)
  7. customdried under vacuum

출처 및 근거

ORD 기록
ord-fc6d7749128a45e783989defb5223586
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07557125B2

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