Diisopropylethylamine → HCID 89426061, compound

HRID 1752435Notes

Reaction equation

HRID 1752435 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[C:4](Cl)[N:3]=1.[NH:13]1[CH2:17][CH2:16][CH2:15][C@H:14]1[C:18]([NH2:20])=[O:19].CCN(C(C)C)C(C)C>C(#N)C>[C:18]([C@@H:14]1[CH2:15][CH2:16][CH2:17][N:13]1[C:4]1[N:3]=[C:2]([Cl:1])[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=1)(=[O:19])[NH2:20]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 111306L-ProlinamideHCID 239689Methyl 2,4-dichloropyrimidine-6-carboxylate

Product 1

HCID 89426061HCID 89426061, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of methyl 2,6-dichloropyrimidine-4-carboxylate (2.074 g, 10.02 mmol) in acetonitrile (50 mL) was added (S)-pyrrolidine-2-carboxamide (1.150 g, 10.07 mmol) and iPr2NEt (1.92 mL, 11.02 mmol). The mixture was heated at 50° C. overnight and then filtered while still warm. The filter cake was washed with acetonitrile (1×10 mL) then dried under vacuum at 40° C. to give a first batch of (S)-methyl 6-(2-carbamoylpyrrolidin-1-yl)-2-chloropyrimidine-4-carboxylate as a tan solid (0.671 g, 2.36 mmol, 24% yield). The filtrate and washes were evaporated in vacuo and triturated with warm acetonitrile (10 mL). The solid was filtered, washed with acetonitrile (2×5 mL), and dried under vacuum at 40° C. to give a second batch of (S)-methyl 6-(2-carbamoylpyrrolidin-1-yl)-2-chloropyrimidine-4-carboxylate as a solid (0.849 g, 2.98 mmol, 30% yield). LC/MS: m/z=285.1 [M+H]+.

Workup

  1. filtrationfiltered
  2. temperaturewhile still warm
  3. washThe filter cake was washed with acetonitrile (1×10 mL)
  4. customthen dried under vacuum at 40° C.

Sources & evidence

ORD record
ord-94fa7a86c9944933ad8dae74d9dfe5ca
Source dataset
uspto-grants-2015_10
Patent number
US09163008B2

Reaction notes

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