Trifluoroacetic acid → 1-(6-Aminopyrimidin-4-yl)-ethanol

HRID 626750Notes

Reaction equation

HRID 626750 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([CH:14]([OH:16])[CH3:15])[N:11]=[CH:10][N:9]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][C:8]1[N:9]=[CH:10][N:11]=[C:12]([CH:14]([OH:16])[CH3:15])[CH:13]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67702244[6-(1-Hydroxyethyl)-pyrimidin-4-yl)-carbamic acid tert-butyl ester

Product 1

HCID 696711341-(6-Aminopyrimidin-4-yl)-ethanolYield 96.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of [6-(1-hydroxyethyl)-pyrimidin-4-yl)-bis-carbamic acid tert-butyl ester and [6-(1-hydroxyethyl)-pyrimidin-4-yl)-carbamic acid tert-butyl ester (200 mg+198 mg, 1.45 mmol) in DCM (6.0 mL) was cooled to 0° C. and TFA (6.0 mL) was added. The reaction mixture was stirred at 0° C. for 15 minutes, then at room temperature for 2 hours. The mixture was concentrated under reduced pressure and the residue was partitioned between saturated aqueous sodium bicarbonate solution and 2-methyltetrahydrofuran (×2). The aqueous layer was then extracted with ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (0-20% methanol in DCM) to afford the title compound as a colorless oil (195 mg, 96% yield). 1H NMR (300 MHz, DMSO-d6): δ 8.60 (s, 1H), 8.54 (br s, 2H), 6.67 (s, 1H), 4.73-4.65 (m, 1H), 1.37 (d, J=6.6 Hz, 3H).

Workup

  1. waitat room temperature for 2 hours
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customthe residue was partitioned between saturated aqueous sodium bicarbonate solution and 2-methyltetrahydrofuran (×2)
  4. extractionThe aqueous layer was then extracted with ethyl acetate
  5. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel flash chromatography (0-20% methanol in DCM)

Sources & evidence

ORD record
ord-82bebb2d098d40218ca1a5e5f6e82bbf
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

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