Crimidine → HCID 67443296, compound

HRID 1666685Notes

Reaction equation

HRID 1666685 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]([CH3:10])[CH3:9])[CH:5]=[C:4]([CH3:11])[N:3]=1.[NH2:12][CH:13]1[CH:17]([OH:18])[CH2:16][N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14]1.C(N(CC)C(C)C)(C)C.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.C(O)CCC>[CH3:9][N:8]([CH3:10])[C:6]1[CH:5]=[C:4]([CH3:11])[N:3]=[C:2]([NH:12][CH:13]2[CH:17]([OH:18])[CH2:16][N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14]2)[N:7]=1

Participants

7

Reactant 4

HCID 10813CrimidineHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 11229445tert-Butyl 3-amino-4-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 67443296HCID 67443296, compoundYield 85.7%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 6212ChloroformSolvent

Procedure

2-Chloro-4-dimethylamino-6-methylpyrimidine (3.5 g), t-butyl (3RS,4RS)-3-amino-4-hydroxypyrrolidine-1-carboxylate (4.5 g), N,N-diisopropylethylamine (5.3 mL), and n-butanol (10 mL) were stirred at 120° C. for 8 days. To the reaction mixture were added chloroform and saturated aqueous sodium hydrogencarbonate to separate the layers. The aqueous layer was extracted with chloroform, then the organic layer was dried with anhydrous sodium sulfate, the desiccant was removed by filtration, and then the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=9:1) to obtain t-butyl (3RS,4RS)-3-(4-dimethylamino-6-methylpyrimidin-2-ylamino)-4-hydroxypyrrolidine-1-carboxylate (5.9 g).

Workup

  1. customto separate the layers
  2. extractionThe aqueous layer was extracted with chloroform
  3. dry with materialthe organic layer was dried with anhydrous sodium sulfate
  4. customthe desiccant was removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (chloroform/methanol=9:1)

Sources & evidence

ORD record
ord-0789fd53271b433d8c2df8b8a75f41db
Source dataset
uspto-grants-2011_10
Patent number
US08044068B2

Reaction notes

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