Ammonia → HCID 66953930, compound

HRID 390083Notes

Reaction equation

HRID 390083 reaction equation
[CH2:1]([O:8][CH2:9][N:10]1[C:18]2[C:17](Cl)=[N:16][CH:15]=[N:14][C:13]=2[C:12]([CH2:20][N:21]([CH3:30])[C@@H:22]([C@H:25]([OH:29])[CH2:26][S:27][CH3:28])[CH2:23][OH:24])=[CH:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:31]>CO>[NH3:10].[NH2:31][C:17]1[C:18]2[N:10]([CH2:9][O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:11]=[C:12]([CH2:20][N:21]([CH3:30])[C@@H:22]([C@H:25]([OH:29])[CH2:26][S:27][CH3:28])[CH2:23][OH:24])[C:13]=2[N:14]=[CH:15][N:16]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 86651334HCID 86651334, compound

Product 2

HCID 222AmmoniaYield 10%HCID 66953930HCID 66953930, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (2R,3S)-2-(((5-(benzyloxymethyl)-4-chloro-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl)(methyl)amino)-4-(methylthio)butane-1,3-diol (240 mg, 0.5 mmol) in 7N NH3 in MeOH (5 ml) was heated in a sealed tube at 140 C (bath temp) overnight. The reaction was concentrated in vacuo and the resulting residue purified by flash chromatography on silica gel eluting with 10%. MeOH/DCM=>10% 7 N NH3 to afford (2R,3S)-2-(((4-amino-5-(benzyloxymethyl)-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl)(methyl)amino)-4-(methylthio)butane-1,3-diol (120 mg, 52%) as a syrup. 1H NMR (CD3OD) δ 8.16 (s, 1H), 7.41 (s, 1H), 7.27 (m, 5H), 5.60 (s, 2H), 4.57 (s, 2H), 4.07 (d, J=15.0 Hz, 1H), 3.82 (m, 3H), 3.71 (dd, J=12.0, 6.0 Hz, 1H), 2.88 (m, 1H), 2.77 (dd, J=15.0, 3.0 Hz, 1H), 2.54 (dd, J=15.0, 6.0 Hz, 1H), 2.43 (s, 3H), 2.03 (s, 3H). 13C NMR (CD3OD) δ 153.2, 151.8, 150.4, 138.2, 134.4, 130.0, 129.7, 129.6, 116.8, 115.3, 79.0, 71.8, 70.8, 67.0, 60.2, 50.0, 40.2, 39.1, 16.8.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customthe resulting residue purified by flash chromatography on silica gel eluting with 10%

Sources & evidence

ORD record
ord-73a5ac098b3745f29aad59124813ade3
Source dataset
uspto-grants-2013_02
Patent number
US08383636B2

Reaction notes

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