Hydrochloric Acid → HCID 46190567, compound

HRID 390095Notes

Reaction equation

HRID 390095 reaction equation
C[C:2]1(C)[O:7][CH:6]([CH2:8][S:9][CH3:10])[CH:5]([CH2:11][N:12]([CH2:14][C:15]2[C:19]3[N:20]=[CH:21][N:22]=[C:23]([NH2:24])[C:18]=3[NH:17][CH:16]=2)[CH3:13])[CH2:4][O:3]1.Cl>CO.C(Cl)Cl>[NH3:12].[CH3:2][OH:3].[NH2:24][C:23]1[C:18]2[NH:17][CH:16]=[C:15]([CH2:14][N:12]([CH2:11][CH:5]([CH:6]([OH:7])[CH2:8][S:9][CH3:10])[CH2:4][OH:3])[CH3:13])[C:19]=2[N:20]=[CH:21][N:22]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 66953959HCID 66953959, compound

Product 2

HCID 21705897Ammonia methanolYield 25%HCID 46190567HCID 46190567, compoundYield 158.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-(((((4RS,5RS)-2,2-dimethyl-4-(methylthiomethyl)-1,3-dioxan-5-yl)methyl)(methyl)amino)methyl)-5H-pyrrolo[3,2-d]pyrimidin-4-amine (34 mg, 93 μmol) in MeOH (2 mL) was added conc aq HCl (0.5 mL) and the solution was allowed to stand at RT for 2 h, then was concentrated to dryness. Chromatography (15% then 25% 7N NH3/MeOH in CH2Cl2) gave (2RS,3RS)-2-((((4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl)(methyl)amino)methyl)-4-(methylthio)butane-1,3-diol (24 mg, 73.7 μmol, 79% yield) as a syrup. 1H NMR (CD3OD) δ 8.16 (1H, s); 7.49 (1H, s); 3.83-3.75 (3H, m); 3.67 (1H, dd, J=5.0, 10.9 Hz); 3.56 (1H, dd, J=7.1, 10.8 Hz); 2.64 (2H, m); 2.57 (1H, dd, J=4.6, 13.6 Hz); 2.41 (1H, dd, J=8.3, 13.5 Hz); 2.34 (3H, s); 2.21-2.12 (1H, m); 2.04 (3H, s). 13C NMR (CD3OD) δ 155.0, 154.0, 150.1, 133.2, 118.2, 115.3, 75.4, 66.3, 61.4, 54.8, 45.9, 45.6, 42.6, 18.9.

Workup

  1. concentrationwas concentrated to dryness

Sources & evidence

ORD record
ord-db83e67a59674de1add80724afd91118
Source dataset
uspto-grants-2013_02
Patent number
US08383636B2

Reaction notes

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