反応 #577233

反応方程式

Carbonic acid 2,2-di-tert-butyl-6-[5-(dimethylamino-methyleneamino)-2-oxo-thiazolo[4,5-d]pyrimidin-3-yl]-tetrahydro-furo[3,2-d][1,3,2]dioxasilin-7-yl ester isopropyl ester

Pyr

→

15

収率 95.0%

Carbonic acid 2-[5-(dimethylamino-methyleneamino)-2-oxo-thiazolo[4,5-d]pyrimidin-3-yl]-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-3-yl ester isopropyl ester

収率 95.0%

溶媒

MeOH

反応条件

後処理

1. 1
   その他The clear colorless reaction
2. 2
   その他The solids were triturated with EtOAc
3. 3
   その他then dried at 40° C

実験手順

Carbonic acid 2,2-di-tert-butyl-6-[5-(dimethylamino-methyleneamino)-2-oxo-thiazolo[4,5-d]pyrimidin-3-yl]-tetrahydro-furo[3,2-d][1,3,2]dioxasilin-7-yl ester isopropyl ester (1.70 g, 2.92 mmol) (14) was dissolved in anhydrous MeOH (10.0 mL) and HF/Pyr (245 uL) was added. The clear colorless reaction suddenly thickened with a white precipitate within 5 min. The reaction was stirred 15 min then conc in vacuo. The solids were triturated with EtOAc then dried at 40° C. 16 h to obtain 1.22 g (95%) of 15 as a flocculent snow white solid: 1H NMR (400 MHz, DMSO-d6) δ 8.72 (1H, s), 8.64 (1H, s), 6.11 (1H, d, J=9.1 Hz), 5.84 (1H, d, J=4.1 Hz), 5.57 (1H, dd, J1=1.2 Hz, J2=3.9 Hz), 4.66-4.74 (2H, m), 4.24-4.28 (2H, m), 4.24-4.28 (1H, m), 3.97-4.01 (1H, m), 3.56-3.73 (2H, m), 3.14 (3H, s), 3.04 (3H, s), 1.18 (3H, dd, J1=0.0 Hz, J2=0.0 Hz), 1.20 (3H, d, J=6.2 Hz), 1.17 (3H, d, J=6.2 Hz); [M+H]+ @ m/z 442.5.

出典