(Diethylamino)sulfur trifluoride → (4-Fluoromethylpyrimidin-2-yl)carbamic acid tert-butyl ester

HRID 626693Notes

Reaction equation

HRID 626693 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[N:13]=[C:12]([CH2:14]O)[CH:11]=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2].CCN(S(F)(F)[F:23])CC>C(Cl)Cl>[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[N:13]=[C:12]([CH2:14][F:23])[CH:11]=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 83854419tert-butyl N-[4-(hydroxymethyl)pyrimidin-2-yl]carbamate

Product 1

HCID 69674809(4-Fluoromethylpyrimidin-2-yl)carbamic acid tert-butyl esterYield 32%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (4-hydroxymethylpyrimidin-2-yl)carbamic acid tert-butyl ester (450 mg, 2.0 mmol) in DCM (10 mL) at 0° C. was treated with DAST (396 μL, 3.0 mmol) and stirred for 10 minutes. The reaction mixture was partitioned between DCM and sodium bicarbonate (sat. aq.). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (50% ethyl acetate in cyclohexane) to afford the title compound as a white solid (144 mg, 32% yield). 1H NMR (300 MHz, CDCl3): δ 8.64 (d, J=5.1 Hz, 1H), 7.53 (s, 1H), 7.15-7.12 (m, 1H), 5.45-5.44 (m, 1H), 5.33-5.32 (m, 1H), 1.54 (s, 9H).

Workup

  1. customThe reaction mixture was partitioned between DCM and sodium bicarbonate (sat. aq.)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel chromatography (50% ethyl acetate in cyclohexane)

Sources & evidence

ORD record
ord-ff0e90e5cb284b07a37a9e21ca5554f3
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

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