Methanol → HCID 67774630, compound

HRID 77280Notes

Reaction equation

HRID 77280 reaction equation
Cl[C:2]1[N:10]=[C:9]([NH:11]C(=O)C2C=CC=CC=2)[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:20]1[O:27][C@H:26]([CH2:28][OH:29])[C@@H:25]([OH:30])[C@:21]21[O:24][CH2:23][CH2:22]2.CO.C[O-].[Na+].[CH:36]1([NH2:39])[CH2:38][CH2:37]1>>[NH2:11][C:9]1[N:8]=[C:7]2[C:3]([N:4]=[CH:5][N:6]2[C@@H:20]2[O:27][C@H:26]([CH2:28][OH:29])[C@@H:25]([OH:30])[C@:21]32[O:24][CH2:23][CH2:22]3)=[C:2]([NH:39][CH:36]2[CH2:38][CH2:37]2)[N:10]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 69828CyclopropylamineHCID 10942334Sodium MethoxideHCID 86665972HCID 86665972, compound

Product 1

HCID 67774630HCID 67774630, compoundYield 76%

Procedure

110 (800 mg, 1.85 mmol) in cyclopropylamine (10 mL) was stirred at room temperature for 24 h. To the solution were added MeOH (10 mL) and 5.4 M NaOMe (1.71 mL, 9.26 mmol) and the resulting mixture was stirred at room temperature for 15 h. The mixture was concentrated in vacuo, and the residue was purified by silica gel column chromatography (0 to 20% MeOH in CH2Cl2) to give 6-cyclopropylamino-nucleoside 111 (500 mg, 76%) as a white solid. 1H NMR (400 MHz, CD3OD) δ: 8.02 (s, 1H), 6.21 (s, 1H), 4.53 (m, 2H), 4.43 (d, 1H, J=8.8 Hz), 3.96 (m, 1H), 3.82-3.77 (m, 2H), 2.91 (m, 1H), 2.56 (m, 1H), 2.27 (m, 1H), 0.83 (m, 2H), 0.60 (m, 2H). LCMS (ESI): 349 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was purified by silica gel column chromatography (0 to 20% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-9e9437196cd0471781ca509724df3e86
Source dataset
uspto-grants-2014_09
Patent number
US08841275B2

Reaction notes

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