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

HRID 1158229Notes

Reaction equation

HRID 1158229 reaction equation
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]

Participants

3

Reactant 2

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

Product 1

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

Conditions

Temperature
80 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b49680ac1e2241cba7a48d34a48cd047
Source dataset
uspto-grants-2010_10
Patent number
US07807832B2

Reaction notes

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