Triethylamine → Tert-butyl 2-(2-aminopyrimidin-4-ylamino)ethylcarbamate

HRID 2401444

反応式

HRID 2401444 の反応式
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[C:5](Br)=[C:4](Cl)[N:3]=1.C(N(CC)CC)C.[H][H]>[Pd].C(OCC)(=O)C.CO>[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:16])([CH3:15])[CH3:17])[CH:5]=[CH:4][N:3]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 86649359Tert-butyl 2-(2-amino-5-bromo-6-chloropyrimidin-4-ylamino)ethylcarbamateHCID 178418361HCID 178418361、化合物

生成物 1

HCID 68602141Tert-butyl 2-(2-aminopyrimidin-4-ylamino)ethylcarbamate

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 21584119Ethylacetate methanol溶媒

実験手順

A solution of tert-butyl 2-(2-amino-5-bromo-6-chloropyrimidin-4-ylamino)ethylcarbamate (Example 1A, 18.60 g, 0.0507 mole), triethylamine (135.0 mL, 0.9686 mole), and 10% palladium on charcoal (7.40 g) in 1:1 ethyl acetate/methanol (500 mL) was treated with hydrogen (60 psi) for two days. Insoluble material was removed by filtration through a pad of diatomaceous earth and the filtrate was concentrated under reduced pressure. The residue was partitioned between ethyl acetate and dilute aqueous sodium hydroxide. The organic layer was dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure to give tert-butyl 2-(2-aminopyrimidin-4-ylamino)ethylcarbamate as a white, amorphous solid (12.7 g, 98.8% yield). 1H NMR (300 MHz, CD3Cl3) δ ppm 1.44 (s, 9H), 3.27-3.37 (m, 2H), 3.37-3.47 (m, 2H), 5.00 (sbr, 2H), 5.28 (sbr, 1H), 5.52 (sbr, 1H), 5.78 (d, J=6 Hz, 1H), 7.76 (d, J=6 Hz, 1H). MS (DCl—NH3) m/z=254 (M+H)+.

後処理

  1. customInsoluble material was removed by filtration through a pad of diatomaceous earth
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was partitioned between ethyl acetate and dilute aqueous sodium hydroxide
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-67d771c486544bfb8e850714a9ea605b
出典データセット
uspto-grants-2014_08
特許番号
US08796297B2

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