Dichloromethane → HCID 178521091, compound

HRID 533192Notes

Reaction equation

HRID 533192 reaction equation
[CH2:1]([N:8]([CH2:30][C@H:31]1[CH2:35][O:34]C(C)(C)[O:32]1)[CH2:9][C:10]1[C:14]2[N:15]=[CH:16][N:17]=[C:18]([O:19]C)[C:13]=2[N:12](COCC2C=CC=CC=2)[CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)Cl>Cl.CO>[CH2:1]([N:8]([CH2:9][C:10]1[C:14]2[N:15]=[CH:16][N:17]=[C:18]([OH:19])[C:13]=2[NH:12][CH:11]=1)[CH2:30][C@H:31]([OH:32])[CH2:35][OH:34])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 67023994HCID 67023994, compound

Product 1

HCID 178521091HCID 178521091, compoundYield 59.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

(S)—N-benzyl-1-(5-(benzyloxymethyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-N-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)methanamine (1.1 g, 2.189 mmol) was heated to 100° C. in HCl (15 ml, 37%) for 3 h. Tlc (CH2Cl2-6M NH3 in MeOH, 9:1) showed reaction over. The solvent was evaporated and the residue dissolved in MeOH, neutralized with Amberlyst A21 resin, filtered and the solvent evaporated. The residue was chromatographed (CH2Cl2-6M NH3 in MeOH, 9:1 then 85:15) to give (S)-3-(benzyl((4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl)amino)propane-1,2-diol (0.427 g, 1.3 mmol, 59.4% yield) as a colourless solid. [α]D20 12.7 (c 0.715, MeOH). The 1H NMR and 13C NMR were identical to that of compound 3.4. +ESMS Found 329.1618 C17H21N4O3 (M+H) requires 329.1614.

Workup

  1. customreaction over
  2. customThe solvent was evaporated
  3. dissolutionthe residue dissolved in MeOH
  4. filtrationfiltered
  5. customthe solvent evaporated
  6. customThe residue was chromatographed (CH2Cl2-6M NH3 in MeOH, 9:1

Sources & evidence

ORD record
ord-0d6767a68fdf42a0b7c76b4fa7867be9
Source dataset
uspto-grants-2014_10
Patent number
US08853224B2

Reaction notes

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