Tert-Butylamine → 2-tert-Butylamino-4-[trimethylsilylethynyl]pyrimidine

HRID 1645291ノート

反応式

HRID 1645291 の反応式
Cl[C:2]1[N:7]=[C:6]([C:8]#[C:9][Si:10]([CH3:13])([CH3:12])[CH3:11])[CH:5]=[CH:4][N:3]=1.[C:14]([NH2:18])([CH3:17])([CH3:16])[CH3:15]>>[C:14]([NH:18][C:2]1[N:7]=[C:6]([C:8]#[C:9][Si:10]([CH3:13])([CH3:12])[CH3:11])[CH:5]=[CH:4][N:3]=1)([CH3:17])([CH3:16])[CH3:15]

参加物

3

反応物 2

HCID 6385Tert-ButylamineHCID 115720232-Chloro-4-(2-(trimethylsilyl)ethynyl)pyrimidine

生成物 1

HCID 121652332-tert-Butylamino-4-[trimethylsilylethynyl]pyrimidine

反応条件

温度
80 °C

実験手順

A mixture of 2-chloro-4-[trimethylsilylethynyl]pyrimidine (25 g, 0.12 mol) and tert-butylamine (100 mL) was heated to 80° C. for 2 d in a sealed tube. The mixture was cooled to rt and triturated with hexanes (100 mL). The resulting white precipitate was filtered and washed with hexanes. The filtrate was concentrated to give the crude product as a brown oil, which was used in the following reaction without further purification. TLC: Rf=0.40. mp 71-73° C. IR: 3293 (br, w), 2962 (w), 1569 (s). 1H NMR: 8.22 (d, J=5.0 Hz, 1H), 6.57 (d, J=5.0 Hz, 1H), 5.19 (s, 1H), 1.42 (s, 9H), 0.26 (s, 9H). 13C NMR: 162.38, 158.15, 150.95, 112.94, 102.77, 97.62, 51.41, 29.25, −0.11. Anal. Calcd for C13H21N3Si: C, 63.11; H, 8.56; N, 16.98. Found: C, 63.20; H, 8.52; N, 16.70.

後処理

  1. temperatureThe mixture was cooled to rt
  2. customtriturated with hexanes (100 mL)
  3. filtrationThe resulting white precipitate was filtered
  4. washwashed with hexanes
  5. concentrationThe filtrate was concentrated

出典と根拠

ORDレコード
ord-13092b12eafb43be912221f96b203a97
出典データセット
uspto-grants-2012_02
特許番号
US08124765B2

反応ノート

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