Diisopropylethylamine → HCID 67209177, compound

HRID 1751191Notes

Reaction equation

HRID 1751191 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6](C(OC(C)(C)C)=O)[CH2:5][CH2:4]1.CCN(C(C)C)C(C)C.Cl[C:26]1[N:31]=[C:30]([C:32]([O:34][CH3:35])=[O:33])[CH:29]=[C:28](Cl)[N:27]=1>C(#N)C>[NH:6]1[CH2:5][CH2:4][CH:3]([CH2:2][NH:1][C:26]2[N:31]=[C:30]([C:32]([O:34][CH3:35])=[O:33])[CH:29]=[CH:28][N:27]=2)[CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 239689Methyl 2,4-dichloropyrimidine-6-carboxylateHCID 7368171-Boc-4-(aminomethyl)piperidine

Product 1

HCID 67209177HCID 67209177, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

Methyl 2-((piperidin-4-ylmethyl)amino)pyrimidine-4-carboxylate was prepared as follows: A 40 mL round-bottomed vial was charged with tert-butyl 4-(aminomethyl)piperidine-1-carboxylate (1.76 mmol, 1.1 equiv.), acetonitrile (4 mL), DiPEA (2.37 mmol, 1.5 equiv.), methyl 2,6-dichloropyrimidine-4-carboxylate (1.58 mmol, 1 equiv.), and then shaken at 85° C. for 72 h. The reaction mixture was concentrated under reduced pressure and purified on SiO2 using a Biotage and a 10-50% EtOAc/hexanes gradient to provide the desired protected amine (233 mg, 552 mg theoretical, 42%). Methyl 2-((piperidin-4-ylmethyl)amino)pyrimidine-4-carboxylate was prepared using the general TFA de-protection procedure and used directly in the general displacement procedure to provide the title compound (4 mg, 73.4 mg theoretical, 5%). LC-MS m/z 456.1 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. custompurified on SiO2 using a Biotage

Sources & evidence

ORD record
ord-c009be0d7fb249b684861f30d909fe50
Source dataset
uspto-grants-2015_10
Patent number
US09157077B2

Reaction notes

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