(Diethylamino)sulfur trifluoride → 2-Chloro-4-(cyclopropyl(fluoro)methyl)pyrimidine

HRID 1039928Notes

Reaction equation

HRID 1039928 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH:8]([CH:10]2[CH2:12][CH2:11]2)O)[CH:5]=[CH:4][N:3]=1.C(N(S(F)(F)[F:19])CC)C>ClCCl>[Cl:1][C:2]1[N:7]=[C:6]([CH:8]([CH:10]2[CH2:12][CH2:11]2)[F:19])[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 77231063(2-Chloropyrimidin-4-yl)(cyclopropyl)methanol

Product 1

HCID 866582382-Chloro-4-(cyclopropyl(fluoro)methyl)pyrimidineYield 26.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2-chloropyrimidin-4-yl)(cyclopropyl)methanol (75 mg, 0.406 mmol) in dichloromethane (2 mL) at 0° C. was added diethylaminosulfur trifluoride (66 mg, 0.410 mmol) and stirred for 30 min. The solution was concentrated to dryness and purified by flash chromatography on silica gel (0-100% EtOAc/hexanes) to afford 2-chloro-4-[cyclopropyl(fluoro)methyl]pyrimidine (20 mg, 0.107 mmol, 26% yield) as a colorless oil. MS ESI: [M+H]+ m/z 187.1. 1H NMR (500 MHz, CDCl3) δ 8.67 (d, J=5.0, 1H), 7.43 (d, J=5.0, 1H), 4.93 (dd, J=7.4, 47.5, 1H), 1.13 (m, 1H), 0.70-0.60 (m, 4H).

Workup

  1. concentrationThe solution was concentrated to dryness
  2. custompurified by flash chromatography on silica gel (0-100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-e51385421e41408a9a9dc0d2d536aa48
Source dataset
uspto-grants-2013_10
Patent number
US08551984B2

Reaction notes

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