HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Triethylamine → 2-(Cyclopentylmethyl)-6-oxo-4-(3-pyridinylamino)-1,6-dihydro-5-pyrimidinecarbonitrile

HRID 1724649
Notes
Print preview

Reaction equation

HRID 1724649 reaction equation
[C:1]([C:3](=[C:8](SC)[NH:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)[C:4]([O:6]C)=O)#[N:2].Cl.[CH:19]1([CH2:24][C:25]([NH2:27])=[NH:26])[CH2:23][CH2:22][CH2:21][CH2:20]1.C(N(CC)CC)C>CN(C=O)C.O>[CH:19]1([CH2:24][C:25]2[NH:27][C:4](=[O:6])[C:3]([C:1]#[N:2])=[C:8]([NH:9][C:10]3[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=3)[N:26]=2)[CH2:23][CH2:22][CH2:21][CH2:20]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 68937763Methyl 2-cyano-3-(methylsulfanyl)-3-(3-pyridinylamino)-2-propenoateHCID 689380642-Cyclopentylethanimidamide hydrochloride

Product 1

HCID 1360559212-(Cyclopentylmethyl)-6-oxo-4-(3-pyridinylamino)-1,6-dihydro-5-pyrimidinecarbonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
100 °C

Procedure

0.1 g (0.40 mmol) of methyl 2-cyano-3-(methylsulfanyl)-3-(3-pyridinylamino)-2-propenoate and 0.065 g (0.40 mmol) of 2-cyclopentylethanamidine hydrochloride and 0.16 g (1.60 mmol) of triethylamine are dissolved in 0.5 ml of DMF and stirred at 100° C. overnight. After cooling, the mixture is diluted with 10 ml of water and extracted with dichloromethane. The organic phase is dried over sodium sulfate and concentrated in vacuo, and the residue is purified by flash chromatography (mobile phase: dichloromethane/methanol 200:1, 100:1, 50:1). 78 mg (64% of theory) of the product are obtained as a colorless solid.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customthe residue is purified by flash chromatography (mobile phase: dichloromethane/methanol 200:1, 100:1, 50:1)
  6. custom78 mg (64% of theory) of the product are obtained as a colorless solid

Sources & evidence

ORD record
ord-5978ce1c15b648e08bc4f627ed4abec8
Source dataset
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07488733B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes