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

HRID 1645291노트

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HRID 1645291 반응식
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]

참가 물질

3

반응물 2

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

생성물 1

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

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온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-13092b12eafb43be912221f96b203a97
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08124765B2

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