Ethyl Acetate → 5-Bromo-2-chloro-N-(tetrahydro-2H-pyran-4-yl)pyrimidin-4-amine

HRID 79110

反応式

HRID 79110 の反応式
[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[O:10]1[CH2:15][CH2:14][CH:13]([NH2:16])[CH2:12][CH2:11]1.C(N(C(C)C)C(C)C)C.C(OCC)(=O)C>O1CCOCC1>[Br:1][C:2]1[C:3]([NH:16][CH:13]2[CH2:14][CH2:15][O:10][CH2:11][CH2:12]2)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 2899735-Bromo-2,4-dichloropyrimidineHCID 4192234-Aminotetrahydropyran

生成物 1

HCID 595508905-Bromo-2-chloro-N-(tetrahydro-2H-pyran-4-yl)pyrimidin-4-amine収率 105.4%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

5-Bromo-2,4-dichloropyrimidine (5.0 g, 21.9 mmol), tetrahydro-2H-pyran-4-amine (2.22 g, 21.9 mmol), and N-ethyl-N-isopropylpropan-2-amine (4.25 g, 32.9 mmol) were dissolved in dioxane (50 ml) and the reaction was stirred at room temperature for 12 hours. Ethyl acetate was added to the reaction mixture and the organic layer was washed with water and brine. The organic layer was dried with sodium sulfate. Removal of solvent gave (5-bromo-2-chloro-pyrimidin-4-yl)-(tetrahydro-pyran-4-yl)-amine (32) as a light yellow solid (6.75 g, 99%). 1H NMR (500 MHz, CD3OD) δ ppm 8.04 (1 H, s), 4.14-4.21 (1 H, m), 3.89 (2 H, dd, J=11.4, 4.3 Hz) 3.43 (2 H, td, J=11.9, 2.0 Hz), 1.80 (2 H, ddd, J=12.6, 4.2, 1.8 Hz), 1.63 (2 H, qd, J=12.2, 4.5, Hz); LCMS-ESI (POS), M/Z, M+1: Found 292.0, Calculated 292.

後処理

  1. washthe organic layer was washed with water and brine
  2. dry with materialThe organic layer was dried with sodium sulfate
  3. customRemoval of solvent

出典と根拠

ORDレコード
ord-350946a916f94333b8163c064f6c4984
出典データセット
uspto-grants-2014_09
特許番号
US08841312B2

関連ノート

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