Di-tert-butyl dicarbonate → tert-Butyl (6-chloro-2-methylpyrimidin-4-yl)carbamate

HRID 69946

Reaction equation

HRID 69946 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH2:9])[CH:3]=1.[O:10](C(OC(C)(C)C)=O)[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=O>C1COCC1.CN(C1C=CN=CC=1)C>[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH:9][C:11](=[O:10])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH:3]=1

Participants

5

Reactant 2

HCID 90495Di-tert-butyl dicarbonateHCID 2867546-Chloro-2-methylpyrimidin-4-amine

Product 1

HCID 86669200tert-Butyl (6-chloro-2-methylpyrimidin-4-yl)carbamateYield 78%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-chloro-2-methylpyrimidin-4-amine (1.0 equiv.) in THF (0.17M) was added BOC2O (1.1 equiv.) and DMAP (cat.). The reaction was allowed to stir overnight, then concentrated to a yellow crude, and filtered through a pad of SiO2 eluting with EtOAc and hexanes (1:1) to afford an off-white solid (78%). LCMS (m/z): 244.1 (MH+); LC Rt=3.69 min.

Workup

  1. concentrationconcentrated to a yellow crude
  2. filtrationfiltered through a pad of SiO2 eluting with EtOAc and hexanes (1:1)

Sources & evidence

ORD record
ord-b14ebb2ce44f4a2aa62d0ea25d21e640
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Linked notes

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