Potassium Phosphate, Tribasic → Methyl 2-chloro-4-cyclopropylpyrimidine-5-carboxylate

HRID 1521535Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1521535
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([C:9]([O:11][CH3:12])=[O:10])=[CH:4][N:3]=1.[CH:13]1(B(O)O)[CH2:15][CH2:14]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1COCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:1][C:2]1[N:7]=[C:6]([CH:13]2[CH2:15][CH2:14]2)[C:5]([C:9]([O:11][CH3:12])=[O:10])=[CH:4][N:3]=1

Komponenten

6

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 2760897Cyclopropylboronic acidHCID 23156323Methyl 2,4-dichloropyrimidine-5-carboxylate

Produkt 1

HCID 83835308Methyl 2-chloro-4-cyclopropylpyrimidine-5-carboxylateAusbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of methyl 2,4-dichloropyrimidine-5-carboxylate (852 mg, 4 mmol) and cyclopropylboronic acid (344 mg, 4 mmol) in THF (10 mL) was added K3PO4 (3.1 g, 12 mmol) followed by Pd(dppf)Cl2 (292 mg, 0.4 mmol) under N2. The mixture was refluxed for 4 h until the material was disappeared. The reaction mixture was cooled to rt. THF was removed under vacuum. Water (20 mL) was added and the mixture was extracted with EtOAc (20 mL×3). The organic layers were dried over anhydrous Na2SO4, filtered and concentrated under vacuum. The residue was purified by preparative TLC to afford methyl 2-chloro-4-cyclopropylpyrimidine-5-carboxylate (220 mg, 26% yield) as a white solid.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 4 h until the material
  2. customTHF was removed under vacuum
  3. additionWater (20 mL) was added
  4. extractionthe mixture was extracted with EtOAc (20 mL×3)
  5. dry with materialThe organic layers were dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe residue was purified by preparative TLC

Quellen und Nachweise

ORD-Eintrag
ord-6e1ab038f14344bbad73474cf674d9b8
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073931B2

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