Diisopropylethylamine → 1,1-dimethylethyl (2S)-2-({[2-chloro-5-(dihydroxyamino)-4-pyrimidinyl]amino}methyl)-1-pyrrolidinecarboxylate

HRID 1366708Notes

Reaction equation

HRID 1366708 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([N:9]([OH:11])[OH:10])=[CH:4][N:3]=1.[NH2:12][CH2:13][C@@H:14]1[CH2:18][CH2:17][CH2:16][N:15]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[C:6]([NH:12][CH2:13][C@@H:14]2[CH2:18][CH2:17][CH2:16][N:15]2[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:5]([N:9]([OH:11])[OH:10])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1512533tert-Butyl (2S)-2-(aminomethyl)pyrrolidine-1-carboxylateHCID 866370362,4-Dichloro-5-(dihydroxyamino)pyrimidine

Product 1

HCID 866370351,1-dimethylethyl (2S)-2-({[2-chloro-5-(dihydroxyamino)-4-pyrimidinyl]amino}methyl)-1-pyrrolidinecarboxylateYield 71.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,4-Dichloro-5-(dihydroxyamino)pyrimidine (2.5 g, 12.75 mmol), 1,1-dimethylethyl (2S)-2-(aminomethyl)-1-pyrrolidinecarboxylate (1.277 g, 6.38 mmol), and DIEA (1.114 mL, 6.38 mmol) were dissolved in DCM (75 mL). The mixture was stirred for 1 h, and when the reaction was complete as determined by LCMS, the solution was concentrated in vacuo. This crude product was purified by flash chromatography (Combiflash, 0-100% ethyl acetate/hexanes) to provide 1,1-dimethylethyl (2S)-2-({[2-chloro-5-(dihydroxyamino)-4-pyrimidinyl]amino}methyl)-1-pyrrolidinecarboxylate (1.6362 g, 71%). LCMS: (M+H)+: 357.8.

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. customThis crude product was purified by flash chromatography (Combiflash, 0-100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-6ebef25e199e47bd924abd55de972d82
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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