2-(Methylsulfonyl)ethanamine → HCID 67520616, compound

HRID 1926095Notes

Reaction equation

HRID 1926095 reaction equation
[O:1]([C:8]1[C:9]2[N:16]([CH2:17][CH:18](O)O)[CH:15]=[CH:14][C:10]=2[N:11]=[CH:12][N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:21][S:22]([CH2:25][CH2:26][NH2:27])(=[O:24])=[O:23].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN(C)C=O.C(O)(=O)C>[CH3:21][S:22]([CH2:25][CH2:26][NH:27][CH2:18][CH2:17][N:16]1[C:9]2[C:8]([O:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[N:13][CH:12]=[N:11][C:10]=2[CH:14]=[CH:15]1)(=[O:24])=[O:23]

Participants

6

Reactant 3

HCID 43405612-(Methylsulfonyl)ethanamineHCID 5049666Sodium triacetoxyborohydrideHCID 56850809HCID 56850809, compound

Product 1

HCID 67520616HCID 67520616, compoundYield 76.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

2-(4-Phenoxy-5H-pyrrolo[3,2-d]pyrimidin-5-yl)ethane-1,1-diol (500 mg) and 2-(methylsulfonyl)ethylamine (341 mg) were dissolved in N,N-dimethylformamide (29 mL)/acetic acid (2.9 mL), and the mixture was stirred at room temperature for 1.5 hrs. Sodium triacetoxyborohydride (579 mg) was added, and the mixture was stirred at room temperature for 16 hrs. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/methanol=100/0→70/30) to give the title compound (508 mg) as a candy-like substance.

Workup

  1. stirringthe mixture was stirred at room temperature for 16 hrs
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (ethyl acetate/methanol=100/0→70/30)

Sources & evidence

ORD record
ord-abcb4f9258fb495bb1d065513b6e0861
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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