Sodium Carbonate → N4-Cyclopentyl-5-iodo-2,4-pyrimidinediamine

HRID 79192

Reaktionsgleichung

Reaktionsgleichung von HRID 79192
[CH:1]1([NH:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH2:13])[N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[I:14]N1C(=O)CCC1=O.C([O-])([O-])=O.[Na+].[Na+].S([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C>[CH:1]1([NH:6][C:7]2[C:12]([I:14])=[CH:11][N:10]=[C:9]([NH2:13])[N:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Komponenten

6

Edukt 4

HCID 10340Sodium CarbonateHCID 24437Sodium SulfiteHCID 120273N-IodosuccinimideHCID 58299890N4-cyclopentylpyrimidine-2,4-diamine

Produkt 1

HCID 58299581N4-Cyclopentyl-5-iodo-2,4-pyrimidinediamineAusbeute 89,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of compound 315 (25.5 g, 143 mmol) in DMF (120 mL) was added N-iodosuccinimide (32 g, 143 mmol) in two portions at rt. The resulting mixture was stirred at rt for 2 h. Upon workup, the mixture was poured into ice and saturated Na2CO3 aqueous solution with some sodium sulfite and extracted with ethyl acetate (2×). The combined organics were washed with saturated Na2CO3 aqueous solution (3×), dried over Na2SO4, and concentrated in vacuo. The residue was subjected to combi-flash column chromatography (methanol/DCM) to give compound 243 (39 g, 73% yield in 2 steps). 1H NMR (500 MHz, DMSO-d6) δ ppm 7.89 (1 H, s), 6.18 (2 H, s), 5.63 (1 H, d, J=7.6 Hz), 4.30 (1 H, sxt, J=7.4 Hz), 1.84-1.96 (2 H, m), 1.61-1.74 (2 H, m), 1.42-1.58 (4 H, m). LCMS-ESI (POS), M/Z, M+1: Found 305.0.

Aufarbeitung

  1. extractionextracted with ethyl acetate (2×)
  2. washThe combined organics were washed with saturated Na2CO3 aqueous solution (3×)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9d0d7e7031ac414990e76121391fb818
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841312B2

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