Diisopropylethylamine → HCID 86672859, compound

HRID 1397044Notes

Reaction equation

HRID 1397044 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[C:4](Cl)[N:3]=1.CCN(C(C)C)C(C)C.[C:22]([O:26][C:27](=[O:36])[NH:28][CH2:29][CH:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)([CH3:25])([CH3:24])[CH3:23]>C1COCC1>[C:22]([O:26][C:27]([NH:28][CH2:29][CH:30]1[CH2:31][CH2:32][N:33]([C:4]2[N:3]=[C:2]([Cl:1])[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=2)[CH2:34][CH2:35]1)=[O:36])([CH3:25])([CH3:23])[CH3:24]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 239689Methyl 2,4-dichloropyrimidine-6-carboxylateHCID 723429Tert-butyl (piperidin-4-ylmethyl)carbamate

Product 1

HCID 86672859HCID 86672859, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 30 mL round-bottomed vial methyl 2,6-dichloropyrimidine-4-carboxylate (300 mg, 1 equiv.) was partially dissolved in anhydrous THF (5 mL). DIEA (278 μL, 1.1 equiv.) was added at once at 0° C. tert-Butyl(piperidin-4-ylmethyl)carbamate (311 mg, 1 equiv.) dissolved in THF (5 mL) was added at 0° C. in 5 min. The reaction mixture was warmed to RT in 3 h15. LC-MS showed mostly the desired product (2.77 min, M+1=385) and a small amount of the other regioisomer (3.28 min, M+1-isobutene=329). The solvent was evaporated and the residue was purified by biotage (SiO2, 10 g, Hex/EtOAc 9:1 to 1:1) to give the desired isomer (386.8 mg, 69.4%) as a white solid. LC-MS m/z 385 (M+1).

Workup

  1. additionwas added at 0° C. in 5 min

Sources & evidence

ORD record
ord-d6e4079f1094496f84e37667d3aa6b4f
Source dataset
uspto-grants-2014_12
Patent number
US08901145B2

Reaction notes

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