Di-tert-butyl dicarbonate → Tert-butyl 6-(2-fluoro-4-nitrophenoxy)pyrimidin-4-ylcarbamate

HRID 1670194Notes

Reaction equation

HRID 1670194 reaction equation
[F:1][C:2]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:3]=1[O:4][C:5]1[N:10]=[CH:9][N:8]=[C:7]([NH2:11])[CH:6]=1.[O:19](C(OC(C)(C)C)=O)[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=O>CN(C1C=CN=CC=1)C.C1COCC1>[F:1][C:2]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:3]=1[O:4][C:5]1[N:10]=[CH:9][N:8]=[C:7]([NH:11][C:20](=[O:19])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH:6]=1

Participants

5

Reactant 2

HCID 90495Di-tert-butyl dicarbonateHCID 231530124-Amino-6-(2-fluoro-4-nitrophenoxy)pyrimidine

Product 1

HCID 59852921Tert-butyl 6-(2-fluoro-4-nitrophenoxy)pyrimidin-4-ylcarbamateYield 26.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 6-(2-fluoro-4-nitrophenoxy)pyrimidin-4-amine (439 mg, 1.2 mmol), BOC2O (261 mg, 1.2 mmol), DMAP (10 mg), and THF (10 mL) was stirred at RT for 1 h then concentrated in vacuo to give the crude product. The product was purified by flash chromatography using 1-2% MeOH in CH2Cl2 as the eluent to give tert-butyl 6-(2-fluoro-4-nitrophenoxy)pyrimidin-4-ylcarbamate as a white solid (110 mg, 26%). 1H NMR (DMSO-d6) δ 10.59 (s, 1H), 8.39 (dd, 1H, J=8.8, 1.1 Hz), 8.32 (dd, 1H, J=10.3, 2.4 Hz), 8.15 (ddd, 1H, J=9.1, 2.5, 1.0 Hz), 7.67 (dd, 1H, J=8.8, 8.8 Hz), 7.45 (s, 1H), 1.44 (s, 9H); MS (ESI−) m/z 349.08 (M−H).

Workup

  1. concentrationthen concentrated in vacuo
  2. customto give the crude product
  3. customThe product was purified by flash chromatography

Sources & evidence

ORD record
ord-0a0fd5cd02844744908f0af3920f443d
Source dataset
uspto-grants-2011_08
Patent number
US07989477B2

Reaction notes

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