Hydrochloric Acid → HCID 24899970, compound

HRID 390076Notes

Reaction equation

HRID 390076 reaction equation
Cl.CC1(C)[O:7][C@H:6]([C@@H:8]([CH2:23][S:24][CH3:25])[CH2:9][N:10]([CH2:12][C:13]2[C:17]3[N:18]=[CH:19][N:20]=[C:21]([NH2:22])[C:16]=3[NH:15][CH:14]=2)[CH3:11])[CH2:5][O:4]1>CO>[NH2:22][C:21]1[C:16]2[NH:15][CH:14]=[C:13]([CH2:12][N:10]([CH3:11])[CH2:9][C@H:8]([CH2:23][S:24][CH3:25])[C@@H:6]([OH:7])[CH2:5][OH:4])[C:17]=2[N:18]=[CH:19][N:20]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66953988HCID 66953988, compound

Product 1

HCID 24899970HCID 24899970, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Concentrated hydrochloric acid (0.5 ml, 178 μmol) was added to a solution of 7-((((S)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-(methylthio)propyl)(methyl)amino)methyl)-5H-pyrrolo[3,2-d]pyrimidin-4-amine (65 mg, 178 μmol) in methanol (5 ml) and the resulting reaction concentrated in vacuo. The resulting residue was purified by flash chromatography on silica gel eluting with 15% 7N NH3 in MeOH/DCM=>20% 7N NH3 in MeOH/DCM to afford (2R,3S)-4-(((4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl)(methyl)amino)-3-(methylthiomethyl)butane-1,2-diol (35 mg, 61% yield) as a syrup. 1H NMR (CD3OD) δ 8.16 (s, 1H), 7.49 (s, 1H), 3.84 (d, J=13.5. Hz, 1H), 3.68 (m, 2H), 3.54 (d, J=4.8 Hz, 2H), 2.70 (m, 2H), 2.53 (dd, J=12.8, 3.8 Hz, 1H), 2.39 (dd, J=13.1, 8.1 Hz, 1H), 2.28 (s, 3H), 2.14 (m, 1H), 2.08 (s, 3H). 13C NMR (CD3OD) 152.5, 151.4, 147.6, 130.6, 115.6, 112.9, 75.4, 65.7, 59.7, 52.0, 42.7, 41.0, 36.0, 16.6.

Workup

  1. customthe resulting reaction
  2. concentrationconcentrated in vacuo
  3. customThe resulting residue was purified by flash chromatography on silica gel eluting with 15% 7N NH3 in MeOH/DCM=>20% 7N NH3 in MeOH/DCM

Sources & evidence

ORD record
ord-064b6d4ef8094332913e00f2380580ca
Source dataset
uspto-grants-2013_02
Patent number
US08383636B2

Reaction notes

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