2-Chloro-4-aminopyrimidine → HCID 118116851, compound

HRID 1774625Notes

Reaction equation

HRID 1774625 reaction equation
[NH:1]1[CH2:5][CH2:4][CH:3]([C:6]([OH:8])=[O:7])[CH2:2]1.Cl[C:10]1[N:15]=[C:14]([NH2:16])[CH:13]=[CH:12][N:11]=1>C(O)(C)C>[NH2:16][C:14]1[CH:13]=[CH:12][N:11]=[C:10]([N:1]2[CH2:5][CH2:4][CH:3]([C:6]([OH:8])=[O:7])[CH2:2]2)[N:15]=1

Participants

4

Reactant 2

HCID 3457522-Chloro-4-aminopyrimidineHCID 30346453-Pyrrolidinecarboxylic acid

Product 1

HCID 118116851HCID 118116851, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

A 100 mL round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with pyrrolidine-3-carboxylic acid (1.20 g, 10 mmol), 2-chloropyrimidin-4-amine (1.30 g, 10 mmol), isopropyl alcohol (IPA, 40 mL), and TEA (6 mL). The mixture was heated at 80° C. overnight (O/N). After this time the reaction was cooled to room temperature (r.t.). It was then filtered and the filter cake was washed with DCM to afford 102a (1.4 g, 67%) as a pale yellow solid. MS: [M+H]+ 209.1

Workup

  1. customA 100 mL round-bottomed flask equipped with a magnetic stirrer and a reflux condenser
  2. temperatureAfter this time the reaction was cooled to room temperature (r.t.)
  3. filtrationIt was then filtered
  4. washthe filter cake was washed with DCM

Sources & evidence

ORD record
ord-19e761e8d5134717bbea8029e3eebc6f
Source dataset
uspto-grants-2016_02
Patent number
US09260415B2

Reaction notes

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