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Diisopropylethylamine → 5-Chloro-2-(4-((6-methoxypyridin-3-yl)methylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)benzonitrile

HRID 657791
ノート
印刷プレビュー

反応式

HRID 657791 の反応式
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH2:9][NH:10][C:11]2[C:12]3[CH2:20][NH:19][CH2:18][CH2:17][C:13]=3[N:14]=[CH:15][N:16]=2)=[CH:5][CH:4]=1.[Cl:21][C:22]1[CH:23]=[CH:24][C:25](F)=[C:26]([CH:29]=1)[C:27]#[N:28].C(N(CC)C(C)C)(C)C.C([O-])(O)=O.[Na+]>CCOC(C)=O.C(#N)C>[Cl:21][C:22]1[CH:23]=[CH:24][C:25]([N:19]2[CH2:18][CH2:17][C:13]3[N:14]=[CH:15][N:16]=[C:11]([NH:10][CH2:9][C:6]4[CH:7]=[N:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=4)[C:12]=3[CH2:20]2)=[C:26]([CH:29]=1)[C:27]#[N:28]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 936535-Chloro-2-fluorobenzonitrile2 回HCID 516892Sodium BicarbonateHCID 59840689N-((6-methoxypyridin-3-yl)methyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-amine

生成物 1

HCID 250624095-Chloro-2-(4-((6-methoxypyridin-3-yl)methylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)benzonitrile収率 44.5%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of N-((6-methoxypyridin-3-yl)methyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-amine (440 mg, 1.6 mmol), 5-chloro-2-fluorobenzonitrile (630 mg, 4.0 mmol), N,N-diisopropylethylamine (560 uL, 3.2 mmol), and acetonitrile (4.0 mL) was subjected to microwave irradiation at 180° C. for 4 h. After that an additional 5-chloro-2-fluorobenzonitrile (400 mg) was added and the mixture was subjected to microwave irradiation at 180° C. for another 2 h. After cooling, the mixture was treated with aq. NaHCO3 and EtOAc (100 mL). The organic layer was separated, washed with brine, dried (Na2SO4), and concentrated in vacuo. The residue was purified by silica gel column (EtOAc: 100%) and the obtained solid was washed with ether to yield an off-white solid (290 mg, 44%).

後処理

  1. customirradiation at 180° C. for 4 h
  2. customirradiation at 180° C. for another 2 h
  3. temperatureAfter cooling
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel column (EtOAc: 100%)
  9. washthe obtained solid was washed with ether

出典と根拠

ORDレコード
ord-459226c8ba004785819a30c1b67ae24d
出典データセット
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08076345B2

反応ノート

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