Diisopropylethylamine → HCID 86672900, compound

HRID 2047634Notes

Reaction equation

HRID 2047634 reaction equation
[CH:1]1([NH:6][CH2:7][C:8]([CH3:14])([CH3:13])[C:9]([NH:11][CH3:12])=[O:10])[CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:15][C:16]1[C:17](Cl)=[N:18][C:19]([Cl:22])=[N:20][CH:21]=1.CCN(C(C)C)C(C)C>CCO>[Br:15][C:16]1[C:17]([N:6]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)[CH2:7][C:8]([CH3:14])([CH3:13])[C:9]([NH:11][CH3:12])=[O:10])=[N:18][C:19]([Cl:22])=[N:20][CH:21]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2899735-Bromo-2,4-dichloropyrimidineHCID 68151242HCID 68151242, compound

Product 1

HCID 86672900HCID 86672900, compoundYield 23.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(cyclopentylamino)-N,2,2-trimethyl-propanamide (665 mg, 3.353 mmol) and 5-bromo-2,4-dichloro-pyrimidine (666 mg, 373.7 μL, 2.921 mmol) were dissolved in EtOH (10 mL) and DIPEA (511.4 mg, 691.9 μL, 3.957 mmol) was added. The reaction was allowed to stir at reflux temperature overnight. The solvent was removed in vacuo. The crude residue was purified by column chromatography (0-100% EtOAc/Petrol) to give the sub-title product as a brown oil (266 mg, 23%); 1H NMR (400.0 MHz, DMSO) d 1.03 (s, 6H), 1.54-1.83 (m, 8H), 2.57 (s, 3H), 3.68 (s, 2H), 4.23 (quin, 1H), 7.53 (d, 1H), 8.63 (s, 1H); MS ES(+) 391.0, ES (−) 389.0.

Workup

  1. temperatureat reflux temperature overnight
  2. customThe solvent was removed in vacuo
  3. customThe crude residue was purified by column chromatography (0-100% EtOAc/Petrol)

Sources & evidence

ORD record
ord-1bdec3637ce645c290fb9f00602d62f1
Source dataset
uspto-grants-2013_11
Patent number
US08592577B2

Reaction notes

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