Acetic Acid → 5-Amino-3-beta-D-ribofuranosyl-3H-thiazolo[4,5-d]pyrimidin-2-one

HRID 549794

반응식

HRID 549794 반응식
[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[S:10][C:9](=[O:11])[N:8]([C@@H:12]3[O:24][C@H:23]([CH2:25][O:26]C(=O)C)[C@@H:18]([O:19]C(=O)C)[C@H:13]3[O:14]C(=O)C)[C:6]=2[N:7]=1.C([O-])([O-])=O.[K+].[K+].CC(O)=O>CO>[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[S:10][C:9](=[O:11])[N:8]([C@@H:12]3[O:24][C@H:23]([CH2:25][OH:26])[C@@H:18]([OH:19])[C@H:13]3[OH:14])[C:6]=2[N:7]=1

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 116332675-Amino-3-(2',3,5'-tri-O-acetyl-beta-D-ribofuranosyl)-3H-thiazolo[4,5-d]pyrimidin-2-one

생성물 1

HCID 101931095-Amino-3-beta-D-ribofuranosyl-3H-thiazolo[4,5-d]pyrimidin-2-one수율 90.1%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of 78 (0.52 g, 1.22 mmol) in MeOH (20 mL) was added K2CO3 (25 mg, 0.18 mmol). The reaction was stirred at room temperature overnight, then neutralized with AcOH (21 μL, 0.36 mmol). The resulting mixture was stirred at room temperature for additional 30 min, concentrated, and triturated with H2O (2 ml) to afford 0.33 g of compound 79 (89%) as a white solid: mp 220° C. (Dec); 1H (400 MHz, d6-DMSO) δ 8.34 (s, 1H), 6.85 (s, 2H), 5.90 (d, J=4.8 Hz, 1H), 5.31 (d, J=5.6 Hz, 1H), 4.98 (d, J=5.6 Hz, 1H), 4.81 (q, J=5.2 Hz, 1H), 4.67 (t, J=6.0 Hz, 1H), 4.11 (q, J=5.2 Hz, 1H), 3.77 (dd, J=10.8, 4.8 Hz, 3H), 358 (m, 1H), 3.44 (m, 1H); MS (+)-ES [M+H]+ m/z 301.1. Elemental Analysis calc'd for C10H12N4O5S.0.3H2O: C, 39.29; H, 4.15; N, 18.33; S10.49. Found: C, 39.51; H, 4.18; N, 17.95; S, 10.27.

후처리

  1. stirringThe resulting mixture was stirred at room temperature for additional 30 min
  2. concentrationconcentrated
  3. customtriturated with H2O (2 ml)

출처 및 근거

ORD 기록
ord-edc077c5ec8a4a1a8568f4b2f2b9bfb8
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07943759B2

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