Diisopropylethylamine → HCID 118483118, compound

HRID 1773340Notes

Reaction equation

HRID 1773340 reaction equation
Cl[C:2]1[N:7]([CH2:8][CH3:9])[C:6](=[O:10])[CH:5]=[C:4]([Cl:11])[N:3]=1.CCN(C(C)C)C(C)C.[C:21]([O:25][C:26]([NH:28][CH:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)=[O:27])([CH3:24])([CH3:23])[CH3:22]>CN(C=O)C>[C:21]([O:25][C:26](=[O:27])[NH:28][CH:29]1[CH2:34][CH2:33][N:32]([C:2]2[N:7]([CH2:8][CH3:9])[C:6](=[O:10])[CH:5]=[C:4]([Cl:11])[N:3]=2)[CH2:31][CH2:30]1)([CH3:24])([CH3:22])[CH3:23]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 7238334-(N-Boc-amino)piperidineHCID 118483166HCID 118483166, compound

Product 1

HCID 118483118HCID 118483118, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2,6-dichloro-3-ethyl-3H-pyrimidin-4-one (320 mg, 1.64 mmol), DIEA (423 mg, 3.28 mmol) and (tert-butoxy)-N-(4-piperidyl)carboxamide (328 mg, 1.64 mmol) in DMF (10 mL) was heated to 120° C. for 1 h. The solvent was concentrated in vacuo and the residue was purified by silica chromatography (1:5, EA:PE) to give 210 mg (36%) of the title compound as a yellow solid. 1H NMR (400 MHz, CDCl3): δ 1.25-1.32 (m 2H), 1.35 (t, J=7.2 Hz, 3H), 1.96-2.02 (m, 2H), 2.98-3.06 (m, 2H), 3.70 (br, 1H), 4.30 (q, J=5.2 Hz, 2H), 4.44 (br, 1H), 4.57-4.61 (m, 2H), 5.95 (s, 1H). [M+H] Calc'd for C16H25ClN4O3, 357, 359. Found, 357, 359.

Workup

  1. concentrationThe solvent was concentrated in vacuo
  2. customthe residue was purified by silica chromatography (1:5, EA:PE)

Sources & evidence

ORD record
ord-3a635ed4dc0d4395848b0cff5efcafa1
Source dataset
uspto-grants-2016_02
Patent number
US09255097B2

Reaction notes

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