Acetyl chloride → HCID 135923795, compound

HRID 533217Notes

Reaction equation

HRID 533217 reaction equation
[OH:1][C:2]1[C:3]2[NH:10][CH:9]=[C:8]([CH2:11][NH:12][CH2:13][CH:14]([CH:18]3[CH2:22][O:21]C(C)(C)[O:19]3)[CH2:15][S:16][CH3:17])[C:4]=2[N:5]=[CH:6][N:7]=1.C(Cl)(=O)C>CO>[OH:19][CH:18]([CH2:22][OH:21])[CH:14]([CH2:15][S:16][CH3:17])[CH2:13][NH:12][CH2:11][C:8]1[C:4]2[N:5]=[CH:6][NH:7][C:2](=[O:1])[C:3]=2[NH:10][CH:9]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 178503721HCID 178503721, compound

Product 1

HCID 135923795HCID 135923795, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirred suspension of N-{4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl}methyl-2-(2,2-dimethyl-1,3-dioxolan-4-yl)-3-(methylthio)propan-1-amine (0.1 g, 0.28 mmol) in methanol (7 ml) was added a solution of acetyl chloride (0.22 g, 2.8 mmol) in methanol (3 ml) and the solution stirred at ambient temperature for 2.5 hr. Amberlyst A-21 resin was added and the solution made neutral before being filtered free of resin and concentrated to a light yellow gum (0.072 g). This was dissolved in aqueous methanol (1:1) and preabsorbed onto silica for chromatography over silica. Gradient elution with DCM/MeOH/0.88 NH3 cocktails ranging from 9:1:0.1 through to 6:4:0.1 in composition furnished the title compound as a precipitate (free base) in the latter fractions. This was recovered by filtration and dried to give a colourless solid (0.026 g). 1H NMR (CD3OD+DCl) δ 7.93 (s, 1H), 7.42 (s, 1H), 3.94 (s, 2H), 3.82 (q, J=4.8 Hz 1H), 3.58 (m, 2H), 2.89 (m, 2H), 2.66 (dd J=13.2, 6.6 Hz, 1H), 2.55 (dd J=13.2, 7.5 Hz, 1H), 2.13 (s, 3H), 1.94 (m, 1H). 13C NMR (CD3OD+DCl) δ 156.6, 145.2, 143.4, 129.1, 119.7, 115.8, 75.0, 65.9, 50.0, 45.9, 41.5, 36.6, 16.3. HR-ESMS MH+ 313.1332 C13H21N4O3S requires MH+ 313.1334 Δ 0.6 ppm.

Workup

  1. additionAmberlyst A-21 resin was added
  2. filtrationbefore being filtered free of resin
  3. concentrationconcentrated to a light yellow gum (0.072 g)
  4. dissolutionThis was dissolved in aqueous methanol (1:1)
  5. custompreabsorbed onto silica for chromatography over silica
  6. washGradient elution with DCM/MeOH/0.88 NH3 cocktails

Sources & evidence

ORD record
ord-b70505902f1d4807892fd5a451e07587
Source dataset
uspto-grants-2014_10
Patent number
US08853224B2

Reaction notes

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