Tris(hydroxymethyl)aminomethane → 2-((5-(benzyloxymethyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methylamino)-2-(hydroxymethyl)propane-1,3-diol

HRID 533193Notes

Reaction equation

HRID 533193 reaction equation
C([BH3-])#N.[Na+].[CH2:5]([O:12][CH2:13][N:14]1[C:22]2[C:21]([O:23][CH3:24])=[N:20][CH:19]=[N:18][C:17]=2[C:16]([CH:25]=O)=[CH:15]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[NH2:27][C:28]([CH2:33][OH:34])([CH2:31][OH:32])[CH2:29][OH:30]>CO>[CH2:5]([O:12][CH2:13][N:14]1[C:22]2[C:21]([O:23][CH3:24])=[N:20][CH:19]=[N:18][C:17]=2[C:16]([CH2:25][NH:27][C:28]([CH2:33][OH:34])([CH2:31][OH:32])[CH2:29][OH:30])=[CH:15]1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 5003444Sodium cyanoborohydrideHCID 577250835-(benzyloxymethyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidine-7-carbaldehyde

Product 1

HCID 252232862-((5-(benzyloxymethyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methylamino)-2-(hydroxymethyl)propane-1,3-diolYield 35.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium cyanoborohydride was added to a suspension of 5-(benzyloxymethyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidine-7-carbaldehyde (50 mg, 168 μmol) and 2-amino-2-(hydroxymethyl)propane-1,3-diol (20.37 mg, 168 μmol) in methanol (5 mL) and stirred overnight at r.t. The crude reaction was absorbed onto silica and eluted with 20% MeOH/EtOAc to afford 2-((5-(benzyloxymethyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methylamino)-2-(hydroxymethyl)propane-1,3-diol (24 mg, 59.6 μmol, 35.5% yield) as a syrup. 1H NMR (d4-MeOH) 8.42 (s, 1H), 7.65 (s, 1H), 7.23 (m, 5H), 5.74 (s, 2H), 4.51 (s, 2H), 4.11 (s, 3H), 4.04 (s, 2H), 3.68 (s, 6H). 13C NMR (d4-MeOH) 158.4, 151.2, 150.9, 139.1, 134.4, 129.7, 129.2, 129.0, 117.5, 116.4, 78.9, 71.9, 62.9, 62.6, 54.8, 36.6.

Workup

  1. customThe crude reaction
  2. customwas absorbed onto silica
  3. washeluted with 20% MeOH/EtOAc

Sources & evidence

ORD record
ord-7bb7c350c4f5446c916bad05dcd94f9b
Source dataset
uspto-grants-2014_10
Patent number
US08853224B2

Reaction notes

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