Ethyl Acetate → HCID 86670087、化合物

HRID 1631701ノート

反応式

HRID 1631701 の反応式
[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[NH:8][C:7](=O)[CH:6]3[CH2:13][O:14][CH2:15][CH2:16][N:5]3[C:4]=2[N:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.[NH4+].[Cl-]>C1COCC1>[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[NH:8][CH2:7][CH:6]3[CH2:13][O:14][CH2:15][CH2:16][N:5]3[C:4]=2[N:3]=1

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 866515602-chloro-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one

生成物 1

HCID 86670087HCID 86670087、化合物収率 59%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

2-Chloro-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one (PREPARATION x1, 17.3 g, 71.9 mmol) was dissolved in THF (250 mL). To the resulting suspension was added lithium aluminum hydride in THF (2.0 M, 46.7 mL, 93 mmol) dropwise through an addition funnel at 0° C. to give a clear light-brown solution. The reaction mixture was allowed to warm to room temperature and was stirred for 3 hours. Ethyl acetate (˜25 mL) was added at 0° C. in portions; a saturated aqueous solution of NH4Cl (125 mL) was then added dropwise until bubbling ceased. The upper organic layer was decanted, concentrated in vacuo and then partitioned between brine and ethyl acetate. The murky bottom layer was then extracted with ethyl acetate (3×) and the combined organic layers were dried over MgSO4, filtered, and concentrated. The product was triturated with ether/ethyl acetate and collected by filtration under nitrogen to give the title compound (9.6 g, 59%). 1H NMR (DMSO-d6) δ 2.88-2.94 (m, 2H), 3.12 (t, 1H), 3.26-3.28 (m, 1H), 3.42-3.51 (m, 2H), 3.86-3.92 (m, 2H), 4.19-4.21 (d, J=8.0 Hz, 1H), 5.96 (br s, 1H), 7.36 (s, 1H). ESI-MS m/z [M+H]+ calc'd for C9H9ClN4O2, 241.04. found 241.1.

後処理

  1. customto give a clear light-brown solution
  2. customuntil bubbling
  3. customThe upper organic layer was decanted
  4. concentrationconcentrated in vacuo
  5. custompartitioned between brine and ethyl acetate
  6. extractionThe murky bottom layer was then extracted with ethyl acetate (3×)
  7. dry with materialthe combined organic layers were dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe product was triturated with ether/ethyl acetate
  11. filtrationcollected by filtration under nitrogen

出典と根拠

ORDレコード
ord-b39402f862fe4b03bd7c55609c9796af
出典データセット
uspto-grants-2014_07
特許番号
US08791107B2

反応ノート

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