Cyclopentylamine → HCID 24937986, compound

HRID 391623Notes

Reaction equation

HRID 391623 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]([O:10]CC)=O)[C:5]([N+:13]([O-])=O)=[C:4]([NH:16][CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[N:3]=1.ClC1N=[C:27]([C:29]([O:31]CC)=O)[C:26]([N+]([O-])=O)=[C:25](Cl)N=1.[CH:38]1(N)[CH2:42]CCC1.C([N:47](C(C)C)CC)(C)C.[O:53]1[CH2:57]CCC1>>[CH:17]1([N:16]2[C:57](=[O:53])[NH:13][C:5]3[C:4]2=[N:3][C:2]([C:26]2[CH:25]=[CH:38][CH:42]=[C:29]([OH:31])[CH:27]=2)=[N:7][C:6]=3[C:8]([NH2:47])=[O:10])[CH2:18][CH2:19][CH2:20][CH2:21]1

Participants

6

Reactant 5

HCID 2906CyclopentylamineHCID 8028Tetrahydrofuran2×HCID 81531DiisopropylethylamineHCID 2761044Ethyl 2,6-dichloro-5-nitropyrimidine-4-carboxylateHCID 57474579HCID 57474579, compound

Product 1

HCID 24937986HCID 24937986, compoundYield 71%

Procedure

Ethyl 2-chloro-6-(cyclopentylamino)-5-nitropyrimidine-4-carboxylate. In a 250 mL round-bottomed flask was placed ethyl 2,6-dichloro-5-nitropyrimidine-4-carboxylate (1.5 g, 5.64 mmol) in tetrahydrofuran (30 mL) and the mixture was cooled down to −78° C. A solution of cyclopentylamine (0.501 mL, 5.07 mmol) and diisopropylethyl amine (0.985 mL, 5.64 mmol) in 4 mL of tetrahydrofuran was added dropwise and the reaction was allowed to warm to room temperature overnight. Solvent was removed under reduced pressure and the crude material was purified by column chromatography (0-2% ethyl acetate in hexanes) to provide the title compound (1.26 g, 4.00 mmol, 71% yield). MS (ESI) m/z 315.2 [M+1]+.

Workup

  1. customIn a 250 mL round-bottomed flask was placed
  2. customSolvent was removed under reduced pressure
  3. customthe crude material was purified by column chromatography (0-2% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-76490ead251c402aa0372e79c2ec2c7d
Source dataset
uspto-grants-2013_02
Patent number
US08383634B2

Reaction notes

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