Hydrochloric Acid → 2-Chloro-7H-pyrrolo[2,3-d]pyrimidine

HRID 475331Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 475331
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH:10]=[CH:9][NH:8][C:6]=2[N:7]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CN(CCN(C)C)C.[BH4-].[Na+].Cl>C1COCC1.COCCOCCOC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[CH:10]=[CH:9][NH:8][C:6]=2[N:7]=1

Komponenten

9

Edukt 5

HCID 313Hydrochloric AcidHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 634876Binap, (A+-)-HCID 4311764Sodium borohydrideHCID 141168712,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine

Produkt 1

HCID 57067742-Chloro-7H-pyrrolo[2,3-d]pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 8028TetrahydrofuranLösungsmittelHCID 8150DiglymeLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine (500 mg, 2.66 mmol), palladium(II)acetate (70 mg, 0.31 mmol) and BINAP (240 mg, 0.39 mmol) are dissolved in 6 mL THF and stirred for 20 min at 20° C. Then TMEDA (300 μL; 2.0 mmol) is added, the mixture is stirred for 20 min and then sodium borohydride (189 mg; 5.11 mmol) dissolved in 10 mL diglyme is added. After 1 h at 20° C. the mixture is combined with 1 N HCl and the solvent is eliminated in vacuo. The residue is purified by column chromatography (method prep. HPLC2; 3% acetonitrile to 55% in 12 min) and 2-chloro-7H-pyrrolo[2,3-d]pyrimidine (HPLC-MS: tRet.=1.25 min; MS(M+H)+=154; method FEC3) is obtained.

Aufarbeitung

  1. stirringthe mixture is stirred for 20 min
  2. additionis added
  3. customThe residue is purified by column chromatography (method prep. HPLC2; 3% acetonitrile to 55% in 12 min)

Quellen und Nachweise

ORD-Eintrag
ord-e27ea18f7072408ca17a6871a18001da
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637549B2

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