Hydrochloric Acid → N-(tetrahydro-2H-pyran-4-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-amine

HRID 2279441ノート

反応式

HRID 2279441 の反応式
[O:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]2[N:9]=[CH:10][C:11]3[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][C:12]=3[N:13]=2)[CH2:3][CH2:2]1.C(Cl)Cl.Cl.O1CCOCC1>CCOCC.CO.CO>[O:1]1[CH2:2][CH2:3][CH:4]([NH:7][C:8]2[N:9]=[CH:10][C:11]3[CH2:17][CH2:16][NH:15][CH2:14][C:12]=3[N:13]=2)[CH2:5][CH2:6]1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 312751,4-DioxaneHCID 68295332tert-butyl 2-(tetrahydro-2H-pyran-4-ylamino)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxylate

生成物 1

HCID 71743546N-(tetrahydro-2H-pyran-4-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-amine収率 77%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 21864698Diethyl ether methanol溶媒

実験手順

A round-bottom flask was charged with 26 (27.5 g, 82.2 mmol), DCM (100 mL) and MeOH (25 mL) and maintained under nitrogen. A 4N solution of HCl in dioxane (103 mL, 411 mmol) was added and the resulting solution stirred for 18 h. The reaction mixture was concentrated and re-suspended in DCM (150 mL). A methanolic NH3 solution (25 mL, 7 N) and additional DCM (100 mL) was added. The precipitated salts were filtered and the filtrate concentrated to afford a brown solid which was stirred with Et2O/MeOH (95:5) for 1 h. A fine light brown solid precipitated and recovered by filtration to afford 15 g, (99% purity, 77% yield) of N-(tetrahydro-2H-pyran-4-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-amine (28): MS m/z (APCI-pos) M+1=235.2.

後処理

  1. temperaturemaintained under nitrogen
  2. concentrationThe reaction mixture was concentrated
  3. additionA methanolic NH3 solution (25 mL, 7 N) and additional DCM (100 mL) was added
  4. filtrationThe precipitated salts were filtered
  5. concentrationthe filtrate concentrated
  6. customto afford a brown solid which
  7. customA fine light brown solid precipitated
  8. filtrationrecovered by filtration

出典と根拠

ORDレコード
ord-b97c92348d5f41d48752b8477de8241e
出典データセット
uspto-grants-2015_09
特許番号
US09133187B2

反応ノート

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