4-Heptanamine → HCID 58298342, compound

HRID 425240Notes

Reaction equation

HRID 425240 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[CH:10]=[C:11]([C:20]#[N:21])[N:12]3[C:17](Cl)=[CH:16][C:15]([CH3:19])=[N:14][C:13]=23)=[C:4]([CH3:22])[CH:3]=1.[CH2:23]([CH:26]([NH2:30])[CH2:27][CH2:28][CH3:29])[CH2:24][CH3:25].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]([CH3:8])[C:5]([C:9]2[CH:10]=[C:11]([C:20]#[N:21])[N:12]3[C:17]([NH:30][CH:26]([CH2:27][CH2:28][CH3:29])[CH2:23][CH2:24][CH3:25])=[CH:16][C:15]([CH3:19])=[N:14][C:13]=23)=[C:4]([CH3:22])[CH:3]=1

Participants

6

Reactant 4

HCID 386654-HeptanamineHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 58298337HCID 58298337, compound

Product 1

HCID 58298342HCID 58298342, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 8-(4-bromo-2,6-dimethyl-phenyl)-4-chloro-2-methyl-pyrrolo[1,2-a]pyrimidine-6-carbonitrile (30.0 g), 1-propyl-butylamine (18.5 g), N,N-diisopropylethylamine (15.5 g) in ethanol (90 mL) was heated at reflux for 2 h. The reaction mixture was cooled to room temperature, poured into a saturated aqueous sodium hydrogencarbonate, and then extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to give a solid. The solid was washed with diisopropylether to give 8-(4-bromo-2,6-dimethyl-phenyl)-2-methyl-4-(1-propyl-butylamino)-pyrrolo[1,2-a]pyrimidine-6-carbonitrile (27.0 g).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customto give a solid
  9. washThe solid was washed with diisopropylether

Sources & evidence

ORD record
ord-0a46d291187c47728b048b5d74e4c735
Source dataset
uspto-grants-2012_01
Patent number
US08106194B2

Reaction notes

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