1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 57929470, compound

HRID 2386668Notes

Reaction equation

HRID 2386668 reaction equation
CCN=C=NCCCN(C)C.[NH:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]=[N:13]1.[CH:21]1([NH:26][C:27]2[C:32]([C:33](O)=[O:34])=[CH:31][N:30]=[C:29]([S:36][CH3:37])[N:28]=2)[CH2:25][CH2:24][CH2:23][CH2:22]1>C(Cl)Cl>[N:12]1([C:33]([C:32]2[C:27]([NH:26][CH:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)=[N:28][C:29]([S:36][CH3:37])=[N:30][CH:31]=2)=[O:34])[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]=[N:13]1

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 223298834-(Cyclopentylamino)-2-(methylsulfanyl)pyrimidine-5-carboxylic acidHCID 178418385HCID 178418385, compound

Product 1

HCID 57929470HCID 57929470, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

EDCI (7.690 g, 40.26 mmol) and benzotriazole (4.796 g, 40.26 mmol) were added to a suspension of 4-cyclopentylamino-2-methylsulfanyl-pyrimidine-5-carboxylic acid (10.186 g, 40.26 mmol) in DCM (250 mL), at RT, and the reaction mixture was stirred for 1 h. The resulting mixture was washed 3 times with water; the combined aqueous extracts were extracted twice with DCM. The combined organic layers were dried over Na2SO4, filtered and evaporated under reduced pressure to give a crude oil. This material was triturated with hot tert-butyl methyl ether and the mixture was left to stand overnight. The white solid which formed was collected by filtration to give 7.698 g (54% yield) of benzotriazol-1-yl-(4-cyclopentylamino-2-methylsulfanyl-pyrimidin-5-yl)-methanone.

Workup

  1. washThe resulting mixture was washed 3 times with water
  2. extractionthe combined aqueous extracts were extracted twice with DCM
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customto give a crude oil
  7. customThis material was triturated with hot tert-butyl methyl ether
  8. waitthe mixture was left
  9. waitto stand overnight
  10. customThe white solid which formed
  11. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-6e2f226c1f3a4ca79af7b82c349c9cf5
Source dataset
uspto-grants-2012_09
Patent number
US08268840B2

Reaction notes

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