4-Heptanamine → HCID 58832865, compound

HRID 902092Notes

Reaction equation

HRID 902092 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[C:11]1[CH:12]=[C:13]([C:22]#[N:23])[N:14]2[C:19](Cl)=[CH:18][C:17]([CH3:21])=[N:16][C:15]=12.[CH2:24]([CH:27]([NH2:31])[CH2:28][CH2:29][CH3:30])[CH2:25][CH3:26].C(N(CC)C(C)C)(C)C.C(=O)([O-])O.[Na+]>C(O)C>[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[C:11]1[CH:12]=[C:13]([C:22]#[N:23])[N:14]2[C:19]([NH:31][CH:27]([CH2:28][CH2:29][CH3:30])[CH2:24][CH2:25][CH3:26])=[CH:18][C:17]([CH3:21])=[N:16][C:15]=12

Participants

6

Reactant 4

HCID 386654-HeptanamineHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 58832867HCID 58832867, compound

Product 1

HCID 58832865HCID 58832865, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 8-(2-bromo-4-isopropyl-phenyl)-4-chloro-2-methyl-pyrrolo[1,2-a]pyrimidine-6-carbonitrile (300 mg), 1-propyl-butylamine (267 mg), N,N-diisopropylethylamine (300 mg) in ethanol (1.0 mL) was heated at reflux overnight. The reaction mixture was cooled to room temperature, poured into a saturated aqueous sodium hydrogencarbonate, and then extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and purified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: hexane/ethyl acetate=20:1) to give 8-(2-bromo-4-isopropyl-phenyl)-2-methyl-4-(1-propyl-butylamino)-pyrrolo[1,2-a]pyrimidine-6-carbonitrile (321 mg) as a pale brown solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. extractionextracted with chloroform
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. custompurified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: hexane/ethyl acetate=20:1)

Sources & evidence

ORD record
ord-8dfcb0089286499aa39eb58904839033
Source dataset
uspto-grants-2008_04
Patent number
US07365078B2

Reaction notes

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