Water → Benzyl 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate

HRID 1052406Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1052406
[Cl:1][C:2]1[C:3]2[C:10](I)=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.C([Li])CCC.[C:17](Cl)(=[O:26])[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>O1CCCC1>[Cl:1][C:2]1[C:3]2[C:10]([C:17]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:26])=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 10387Benzyl chloroformateHCID 148092816-Chloro-7-iodo-7-deazapurineHCID 178418339Butyllithium

Produkt 1

HCID 118433776Benzyl 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylateAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

In a three-neck reactor 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (1 g, 3.58 mmol) was dissolved in 36 mL tetrahydrofuran. The mixture was cooled at −78° C. and butyllithium solution (2.5 M in hexane, 3.20 mL, 8 mmol) dissolved in 10 mL was added dropwise over 15 min. The reaction was stirred at −78° C. for 20 min. Then benzyl carbonochloridate (570 μl, 3.99 mmol) was added dropwise. The reaction was stirred overnight. Water was added and the mixture evaporated. The crude was partitioned between ethyl acetate and water, brine, dried over sodium sulphate, filtered and concentrated under reduced pressure. The residue was purified using SP1® Purification System (0% to 20%, hexane-ethyl acetate) to give 490 mg (48% yield) of the title compound. Purity 100%.

Aufarbeitung

  1. additionwas added dropwise over 15 min
  2. stirringThe reaction was stirred overnight
  3. customthe mixture evaporated
  4. customThe crude was partitioned between ethyl acetate and water, brine
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified
  9. customSP1® Purification System (0% to 20%, hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-f18f644a6ea047618cb2e870a687c952
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09388189B2

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