Diisopropylethylamine → HCID 54013611, compound

HRID 522648Notes

Reaction equation

HRID 522648 reaction equation
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(N(C(C)C)CC)(C)C.Cl[C:24]1[N:29]=[CH:28][C:27]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:26][N:25]=1>ClCCl>[C:10]([O:9][C:7]([N:1]1[CH2:6][CH2:5][N:4]([C:24]2[N:25]=[CH:26][C:27]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:28][N:29]=2)[CH2:3][CH2:2]1)=[O:8])([CH3:13])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 104878152-Chloro-pyrimidine-5-carboxylic acid ethyl ester

Product 1

HCID 54013611HCID 54013611, compoundYield 119.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl piperazine-1-carboxylate (7.9 g, 42.5 mmol) and diisopropylethylamine (13.69 g, 106.1 mmol) in dichloromethane (80 mL) was added ethyl 2-chloropyrimidine-5-carboxylate (7.9 g, 42.5 mmoL), and the reaction mixture was stirred at room temperature for 3 hours. LCMS showed the reaction was completed. The reaction mixture was directly concentrated to afford ethyl 2-(4-(tert-butoxycarbonyl)piperazin-1-yl)pyrimidine-5-carboxylate (17 g, crude), which was directly used in the next step without further purification. MS (ES+) C16H24N4O4 requires: 336, found: 237, 281 [M-56+H]+.

Workup

  1. concentrationThe reaction mixture was directly concentrated

Sources & evidence

ORD record
ord-e75d4f60a6b84067be9a70ffdc9bfaf9
Source dataset
uspto-grants-2016_05
Patent number
US09334263B2

Reaction notes

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