1,3-Dioxolane-4-methanol → tetrahydro-3-furanyl N-[4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]carbamate

HRID 51550

Reaktionsgleichung

Reaktionsgleichung von HRID 51550
[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:26])[O:19][C:20]4[CH:25]=CC=[CH:22][CH:21]=4)=[C:13]([O:27][CH3:28])[CH:12]=3)=[CH:9][N:8]([CH:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)[C:4]=2[N:5]=[CH:6][N:7]=1.C1OC[O:37]C1CO>N1C=CC=CC=1>[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:26])[O:19][CH:20]4[CH2:21][CH2:22][O:37][CH2:25]4)=[C:13]([O:27][CH3:28])[CH:12]=3)=[CH:9][N:8]([CH:29]3[CH2:30][CH2:31][O:32][CH2:33][CH2:34]3)[C:4]=2[N:5]=[CH:6][N:7]=1

Komponenten

4

Edukt 2

HCID 216181,3-Dioxolane-4-methanolHCID 22736249phenyl N-[4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]carbamate

Produkt 1

HCID 22736289tetrahydro-3-furanyl N-[4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Phenyl N-[4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]carbamate (30 mg, 0.065 mmol) was mixed glycerol formal (0.05 mL) in pyridine (0.5 mL). The reaction mixture was heated at 100° C. overnight. The solvent was removed and the residue was purified by preparative reverse phase PHLC to give tetrahydro-3-furanyl N-[4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]carbamate (2 mg, 0.004 mmol). 1H NMR (CDCl-d) δ 2.06(m, 4H), 3.66(m, 2H), 3.92(m, 3H), 4.07(m, 6H), 4.79(m, 1H), 4.83(d, J=6.3 Hz, 1H), 4.96(m, 1H), 5.04(d, J=6.3 Hz, 1H), 6.15(vbs, 2H), 6.96 (s, 1H), 7.05(m, 2H), 7.53(s, 1H), 8.15(d, J=8.2 Hz, 1H), 8.22(s, 1H). LC/MS MH30 =471 and 1,3-dioxolan-4-ylmethyl N-(4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl)carbamate(6.0 mg, 0.013 mmol). 1H NMR (CDCl-d) δ 2.06(m, 4H), 3.66(m, 2H), 3.75(m, 1H), 3.92(m, 3H), 4.03(m, 1H), 4.13(m, 1H), 4.34(m, 2H), 4.94(s, 1H), 4.97(m, 1H), 5.10(s, 1H), 5.32(bs, 2H), 6.97(s, 1H), 7.03 (m, 2H), 7.06(d, J=8.2 Hz, 1H), 7.38(s, 1H), 8.15(d, J=7.9 Hz, 1H), 8.31(s, 1H). LC/MS MH30 =471.

Aufarbeitung

  1. customThe solvent was removed
  2. customthe residue was purified by preparative reverse phase PHLC

Quellen und Nachweise

ORD-Eintrag
ord-9cca8422583e47bc85f38c4d96a347fe
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713474B2

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