tert-butyl N-(prop-2-yn-1-yl)carbamate → tert-Butyl 3-(2-amino-4-chloro-6-methylpyrimidin-5-yl)prop-2-ynylcarbamate

HRID 2387792ノート

反応式

HRID 2387792 の反応式
[CH2:1]([NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[C:2]#[CH:3].[Cl:12][C:13]1[C:18](I)=[C:17]([CH3:20])[N:16]=[C:15]([NH2:21])[N:14]=1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:21][C:15]1[N:14]=[C:13]([Cl:12])[C:18]([C:3]#[C:2][CH2:1][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:8])([CH3:10])[CH3:9])=[C:17]([CH3:20])[N:16]=1

参加物

4

反応物 2

HCID 11073648tert-butyl N-(prop-2-yn-1-yl)carbamateHCID 116447204-Chloro-5-iodo-6-methylpyrimidin-2-amine

生成物 1

HCID 86633394tert-Butyl 3-(2-amino-4-chloro-6-methylpyrimidin-5-yl)prop-2-ynylcarbamate収率 46.9%

試薬・触媒・溶媒 1

HCID 178418476HCID 178418476、化合物触媒

反応条件

温度
70 °C

実験手順

tert-Butyl prop-2-ynylcarbamate (3.11 g), 4-chloro-5-iodo-6-methylpyrimidin-2-amine (1.8 g) and bis(triphenylphosphine)palladium(II) chloride (0.469 g) were combined in TEA (100 mL). The reaction mixture was purged with nitrogen gas for 3 min then copper(I) iodide (0.254 g) added. The resulting mixture was stirred at 70° C. for 16 h, then cooled to rt and filtered. The filtrate was washed with water and brine, dried and the solvents evaporated. The crude material was dissolved in MeOH (20 mL), acidified with acetic acid (1 mL) and purified by SCX and further purified by chromatography eluting 10% MeOH and 0.25% Ammonia (7N) in DCM to afford the subtitle compound 0.93 g.

後処理

  1. customThe reaction mixture was purged with nitrogen gas for 3 min
  2. additioncopper(I) iodide (0.254 g) added
  3. temperaturecooled to rt
  4. filtrationfiltered
  5. washThe filtrate was washed with water and brine
  6. customdried
  7. customthe solvents evaporated
  8. dissolutionThe crude material was dissolved in MeOH (20 mL)
  9. custompurified by SCX
  10. customfurther purified by chromatography
  11. washeluting 10% MeOH and 0.25% Ammonia (7N) in DCM

出典と根拠

ORDレコード
ord-ce8b34d27d964b58a6fc7a7c1604ab2a
出典データセット
uspto-grants-2012_09
特許番号
US08268990B2

反応ノート

読み込み中…