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

HRID 1521535노트

반응식

HRID 1521535 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6e1ab038f14344bbad73474cf674d9b8
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073931B2

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