Dichloromethane → HCID 178521092, compound

HRID 533187Notes

Reaction equation

HRID 533187 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 58287034(R)-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

Product 1

HCID 178521092HCID 178521092, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

(R)—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 (0.6 g, 1.194 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 (R)-3-(benzyl((4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl)amino)propane-1,2-diol (0.36 g, 1.096 mmol, 92% yield) as a colourless solid. [α]D22 +13.0 (c 0.715, MeOH). 1H NMR (CD3OD, 300 MHz), δ ppm, 7.90 (s, 1H), 7.37 (s, 1H), 7.31-7.16 (m, 5H), 3.97-3.78 (m, 3H), 3.69 (d, 1H, J 13.8 Hz), 3.63 (d, 1H, J 13.8 Hz), 3.50 (dd, 1H, J 11.2, 4.8 Hz), 3.42 (dd, 1H, J 11.2, 5.7 Hz), 2.60 (d, 2H, J 6.4 Hz). 13C NMR (CD3OD, 75.5 MHz), δ ppm, 156.1 (C), 145.5 (C), 142.5 (CH), 140.2 (C), 130.2 (CH), 129.4 (CH), 129.2 (CH), 128.1 (CH), 119.3 (C), 115.0 (C), 70.6 (CH), 66.3 (CH2), 60.0 (CH2), 57.6 (CH2), 49.0 (CH2). +ESMS Found 329.1600 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-9f650a4bdd2143f48a94893dea629ea5
Source dataset
uspto-grants-2014_10
Patent number
US08853224B2

Reaction notes

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