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Diisopropylethylamine → 4-(4-carbamoyl-1,2,3,6-tetrahydropyridin-1-yl)-2,5-dimethyl-7-(4-isopropyl-2-methylthiophenyl)-7H-pyrrolo [2,3-d]pyrimidine

HRID 1359489
Notes
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Reaction equation

HRID 1359489 reaction equation
FC(F)(F)C(O)=O.[C:8]([C:11]1[CH2:12][CH2:13][NH:14][CH2:15][CH:16]=1)(=[O:10])[NH2:9].Cl[C:18]1[C:19]2[C:27]([CH3:28])=[CH:26][N:25]([C:29]3[C:33]([CH:34]([CH3:36])C)=[CH:32][S:31][C:30]=3[CH3:37])[C:20]=2[N:21]=[C:22]([CH3:24])[N:23]=1.[CH:38](N(C(C)C)CC)([CH3:40])[CH3:39].C(=O)([O-])O.[Na+]>C(O)C>[C:8]([C:11]1[CH2:16][CH2:15][N:14]([C:18]2[C:19]3[C:27]([CH3:28])=[CH:26][N:25]([C:29]4[CH:33]=[CH:34][C:36]([CH:38]([CH3:40])[CH3:39])=[CH:37][C:30]=4[S:31][CH3:32])[C:20]=3[N:21]=[C:22]([CH3:24])[N:23]=2)[CH2:13][CH:12]=1)(=[O:10])[NH2:9]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 224827414-Carbamoyl-1,2,3,6-tetrahydropyridine trifluoroacetateHCID 865899054-chloro-2,5-dimethyl-7-(isopropyl-2-methylthiophenyl)-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 159078794-(4-carbamoyl-1,2,3,6-tetrahydropyridin-1-yl)-2,5-dimethyl-7-(4-isopropyl-2-methylthiophenyl)-7H-pyrrolo [2,3-d]pyrimidine
Yield 37.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 4 ml of ethanol, 0.25 g of 4-carbamoyl-1,2,3,6-tetrahydropyridine trifluoroacetate and 0.35 g of 4-chloro-2,5-dimethyl-7-(isopropyl-2-methylthiophenyl)-7H-pyrrolo[2,3-d]pyrimidine were dissolved, and 0.39 g of diisopropylethylamine were added thereto. The reaction mixture was heated under reflux for 7.5 hours, and subsequently, a saturated aqueous solution of sodium hydrogencarbonate was poured into the reaction mixture. The reaction mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and subsequently dried over anhydrous sodium sulfate. After the desiccant was filtered off, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform—methanol=60:1), followed by crystallization from a mixed solvent of ethyl acetate-diethyl ether to yield 0.17 g of 4-(4-carbamoyl-1,2,3,6-tetrahydropyridin-1-yl)-2,5-dimethyl-7-(4-isopropyl-2-methylthiophenyl)-7H-pyrrolo [2,3-d]pyrimidine.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 7.5 hours
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialsubsequently dried over anhydrous sodium sulfate
  6. filtrationAfter the desiccant was filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluent: chloroform—methanol=60:1)
  9. customfollowed by crystallization from a mixed solvent of ethyl acetate-diethyl ether

Sources & evidence

ORD record
ord-4cc1272895bf48348cd9913ea4d4aaf4
Source dataset
uspto-grants-2003_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06600038B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes