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

HRID 225890ノート

反応式

HRID 225890 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-fc6d7749128a45e783989defb5223586
出典データセット
uspto-grants-2009_07
特許番号
US07557125B2

反応ノート

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