6-chloro-2-N,4-N-dipropyl-1,3,5-triazine-2,4-diamine → 6-[1,2]oxazinan-2-yl-N,N'-dipropyl-[1,3,5]triazine-2,4-diamine

HRID 530060ノート

反応式

HRID 530060 の反応式
Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][CH3:11])[N:5]=[C:4]([NH:12][CH2:13][CH2:14][CH3:15])[N:3]=1.C(N(C(C)C)C(C)C)C.Cl.[O:26]1[CH2:31][CH2:30][CH2:29][CH2:28][NH:27]1.C([O-])(O)=O.[Na+]>O1CCCC1>[O:26]1[CH2:31][CH2:30][CH2:29][CH2:28][N:27]1[C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][CH3:11])[N:5]=[C:4]([NH:12][CH2:13][CH2:14][CH3:15])[N:3]=1

参加物

6

反応物 4

HCID 183046-chloro-2-N,4-N-dipropyl-1,3,5-triazine-2,4-diamineHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 130107121,2-Oxazinane hydrochloride

生成物 1

HCID 573779086-[1,2]oxazinan-2-yl-N,N'-dipropyl-[1,3,5]triazine-2,4-diamine収率 89%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
100 °C

実験手順

An ACE® pressure tube was charged with 2-chloro-N-(4,6-bis-(n-propylamino)-[1,3,5]triazine (XXXIV) (1.50 g, 6.53 mmol), N-ethyldiisopropylamine (19.59 mmol), 1,2-oxazinane hydrochloride (1.61 g, 13.06 mmol) and tetrahydrofuran. The reaction mixture was heated at 100° C. for 2 h, then cooled and poured into saturated NaHCO3 solution (50 mL). The suspension was extracted with EtOAc (3×25 mL). The combined organic extracts were washed with water (50 mL), brine (50 mL) and dried over Na2SO4. The solvent was removed under reduced pressure and the crude product was purified by flash column chromatography using gradient elution from CH2Cl2/EtOH (99:1) to CH2Cl2/EtOH (95:5) to yield 6-[1,2]oxazinan-2-yl-N,N′-dipropyl-[1,3,5]triazine-2,4-diamine (LVII) (1.63 g, 89%). ESI-MS (m/z): 281 [M+H]+.

後処理

  1. temperaturecooled
  2. extractionThe suspension was extracted with EtOAc (3×25 mL)
  3. washThe combined organic extracts were washed with water (50 mL), brine (50 mL)
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed under reduced pressure
  6. customthe crude product was purified by flash column chromatography
  7. washelution from CH2Cl2/EtOH (99:1) to CH2Cl2/EtOH (95:5)

出典と根拠

ORDレコード
ord-05129805e29540849e1a872ada95a143
出典データセット
uspto-grants-2016_05
特許番号
US09351972B2

反応ノート

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