2,4,5,6-Tetrachloropyrimidine → HCID 23577269, compound

HRID 1827142Notes

Reaction equation

HRID 1827142 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:5][CH2:4]1.C(N(CC)C(C)C)(C)C.Cl[C:29]1[N:34]=[C:33]([Cl:35])[N:32]=[C:31]([Cl:36])[C:30]=1[Cl:37]>C1COCC1>[CH2:12]([O:11][C:9]([N:6]1[CH2:7][CH2:8][CH:3]([CH2:2][NH:1][C:29]2[C:30]([Cl:37])=[C:31]([Cl:36])[N:32]=[C:33]([Cl:35])[N:34]=2)[CH2:4][CH2:5]1)=[O:10])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 156902,4,5,6-TetrachloropyrimidineHCID 81531DiisopropylethylamineHCID 219554994-Aminomethyl-1-N-Cbz-piperidine

Product 1

HCID 23577269HCID 23577269, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzyl 4-(aminomethyl)piperidine-1-carboxylate (EXAMPLE 13, Step 1) and N,N-diisopropylethylamine (2.6 g, 20 mmol) in THF (40 mL) at −78° C. was added a solution of tetrachloropyrimidine (4.4 g, 20 mmol). The cooling bath was removed and the solution was stirred for 45 min. The solution was concentrated and purified by filtering through a pad of silica gel using ether.

Workup

  1. customThe cooling bath was removed
  2. concentrationThe solution was concentrated
  3. custompurified
  4. filtrationby filtering through a pad of silica gel

Sources & evidence

ORD record
ord-ea031949b0034388a2214da73d877f93
Source dataset
uspto-grants-2006_05
Patent number
US07053089B2

Reaction notes

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