Pyrimidine, 2,4-dichloro-5-methyl- → HCID 86713603, compound

HRID 524086Notes

Reaction equation

HRID 524086 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([CH3:9])=[CH:4][N:3]=1.[N:10]1([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.CCN(C(C)C)C(C)C>CN(C=O)C.O>[Cl:1][C:2]1[N:7]=[C:6]([N:13]2[CH2:12][CH2:11][N:10]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH2:14]2)[C:5]([CH3:9])=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 74508Pyrimidine, 2,4-dichloro-5-methyl-HCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 86713603HCID 86713603, compoundYield 96.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,4-dichloro-5-methylpyrimidine (0.75 g, 4.6 mmol) in dry DMF (15.5 mL) was added tert-butyl piperazine-1-carboxylate (0.9 g, 4.85 mmol) followed by DIEA (0.91 mL, 5.5 mmol) at 0° C., and the mixture was stirred to room temperature overnight. LCMS showed the reaction was completed. The reaction was diluted with water (120 mL), and the solid was filtered. The residue was washed with water and dried to give the title compound (1.386 g, 96%) as a white solid. MS (ES+) C14H21ClN4O2 requires: 312. found: 313 [M+H]+

Workup

  1. filtrationthe solid was filtered
  2. washThe residue was washed with water
  3. customdried

Sources & evidence

ORD record
ord-690c8322ac664b05b4b195c448f11d8d
Source dataset
uspto-grants-2016_05
Patent number
US09340514B2

Reaction notes

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