Triethylamine → Ethyl 1-[(pyrimidin-5-ylcarbonyl)amino]-cyclopropanecarboxylate

HRID 1406327Notes

Reaction equation

HRID 1406327 reaction equation
[N:1]1[CH:6]=[C:5]([C:7]([OH:9])=O)[CH:4]=[N:3][CH:2]=1.C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.Cl.[NH2:40][C:41]1([C:44]([O:46][CH2:47][CH3:48])=[O:45])[CH2:43][CH2:42]1>C1COCC1>[N:3]1[CH:4]=[C:5]([C:7]([NH:40][C:41]2([C:44]([O:46][CH2:47][CH3:48])=[O:45])[CH2:43][CH2:42]2)=[O:9])[CH:6]=[N:1][CH:2]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 78346Pyrimidine-5-carboxylic acidHCID 386203Ethyl 1-aminocyclopropane-1-carboxylate hydrochlorideHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 67444517Ethyl 1-[(pyrimidin-5-ylcarbonyl)amino]-cyclopropanecarboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6.80 g (54.8 mmol) of pyrimidine-5-carboxylic acid, 18.82 mL (135 mmol) of triethylamine and 19.27 g (60 mmol) of TBTU in 200 mL THF was stirred for 30 minutes at ambient temperature. Then 9.11 g (55 mmol) of ethyl 1-amino-cyclopropanecarboxylate hydrochloride were added and the mixture was stirred further overnight. Then the mixture was evaporated down, the residue was stirred with 200 mL water and the crude product was extracted with ethyl acetate. The intermediate product was purified by column chromatography (silica gel, dichloromethane+0-4% methanol).

Workup

  1. customThen the mixture was evaporated down
  2. stirringthe residue was stirred with 200 mL water
  3. extractionthe crude product was extracted with ethyl acetate
  4. customThe intermediate product was purified by column chromatography (silica gel, dichloromethane+0-4% methanol)

Sources & evidence

ORD record
ord-0cad9dd7ec1b4577ba7779f901bdfff9
Source dataset
uspto-grants-2014_12
Patent number
US08916589B2

Reaction notes

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