Ethylamine hydrochloride → HCID 86762625, compound

HRID 2409061Notes

Reaction equation

HRID 2409061 reaction equation
[CH3:1][Si:2]([CH3:20])([CH3:19])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[C:15]2[CH:14]=[N:13][C:12]([C:16](=O)[CH3:17])=[N:11][C:10]=2[CH:9]=[CH:8]1.Cl.[CH2:22]([NH2:24])[CH3:23].C([BH3-])#N.[Na+]>CCO>[CH2:22]([NH:24][CH:16]([C:12]1[N:13]=[CH:14][C:15]2[N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:20])([CH3:19])[CH3:1])[CH:8]=[CH:9][C:10]=2[N:11]=1)[CH3:17])[CH3:23]

Participants

5

Reactant 3

HCID 11198Ethylamine hydrochlorideHCID 5003444Sodium cyanoborohydrideHCID 86762624HCID 86762624, compound

Product 1

HCID 86762625HCID 86762625, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
130 °C

Procedure

A microwave vial charged with 1-(5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-d]pyrimidin-2-yl)ethanone (1.50 g, 5.15 mmol), ethylamine hydrochloride (3.36 g, 41.2 mol), sodium cyanoborohydride (420.5 mg, 6.69 mmol), and anhydrous EtOH (40 mL) was stirred under microwave irradiation (300 Watts) at 130° C. for 2 min. The solid was filtered and rinsed well with EtOH. Volatile solvent from the filtrate was removed under reduced pressure. The resultant crude was redissolved in EtOAc and washed with 10% aqueous NaOH solution (2×), water, and brine. The organic phase was dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude was triturated in DCM, and the insoluble solid was filtered through a pad of Celite®. The filtrate was concentrated under reduced pressure and dried on high-vac to afford N-ethyl-1-(5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-d]pyrimidin-2-yl)ethanamine as an oil. 1H NMR (400 MHz, CDCl3) δ 8.92 (s, 1H), 7.50 (d, J=3.2 Hz, 1H), 6.65 (d, J=3.2 Hz, 1H), 5.50 (s, 2H), 4.09 (q, J=6.7 Hz, 1H), 3.46 (t, J=8.1 Hz, 2H), 2.57 (dd, J=11.2, 7.2 Hz, 1H), 2.46 (dd, J=11.2, 7.0 Hz, 1H), 2.08 (br s, 1H), 1.46 (d, J=6.7 Hz, 3H), 1.08 (t, J=7.1 Hz, 3H), 0.88 (t, J=8.1 Hz, 2H), −0.07 (d, J=0.9 Hz, 9H)); MS (ESI) m/z: 321.4 [M+1]+.

Workup

  1. filtrationThe solid was filtered
  2. washrinsed well with EtOH
  3. customVolatile solvent from the filtrate was removed under reduced pressure
  4. dissolutionThe resultant crude was redissolved in EtOAc
  5. washwashed with 10% aqueous NaOH solution (2×), water, and brine
  6. dry with materialThe organic phase was dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude was triturated in DCM
  10. filtrationthe insoluble solid was filtered through a pad of Celite®
  11. concentrationThe filtrate was concentrated under reduced pressure
  12. customdried on high-vac

Sources & evidence

ORD record
ord-2d60c20fc30b482e8cf690cec101c5a9
Source dataset
uspto-grants-2014_08
Patent number
US08815877B2

Reaction notes

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