Potassium Carbonate → 2-(4-Chloro-5-oxazol-5-yl-pyrrolo[2,3-d]pyrimidin-7-yl)-5-hydroxymethyl-3-methyl-tetrahydro-furan-3,4-diol

반응식

[Cl:1][C:2]1[C:3]2[C:10]([CH:11]=[O:12])=[CH:9][N:8]([CH:13]3[C:17]([OH:19])([CH3:18])[CH:16]([OH:20])[CH:15]([CH2:21][OH:22])[O:14]3)[C:4]=2[N:5]=[CH:6][N:7]=1.S([CH2:33][N+:34]#[C-:35])(C1C=CC(C)=CC=1)(=O)=O.C([O-])([O-])=O.[K+].[K+]>>[Cl:1][C:2]1[C:3]2[C:10]([C:11]3[O:12][CH:35]=[N:34][CH:33]=3)=[CH:9][N:8]([CH:13]3[C:17]([CH3:18])([OH:19])[CH:16]([OH:20])[CH:15]([CH2:21][OH:22])[O:14]3)[C:4]=2[N:5]=[CH:6][N:7]=1

참가 물질

반응물 3

HCID 11430Potassium Carbonate

HCID 161915Tosylmethyl isocyanide

HCID 210408384-Chloro-7-(3,4-dihydroxy-5-hydroxymethyl-3-methyl-tetrahydrofuran-2-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbaldehyde

생성물 1

HCID 866235892-(4-Chloro-5-oxazol-5-yl-pyrrolo[2,3-d]pyrimidin-7-yl)-5-hydroxymethyl-3-methyl-tetrahydro-furan-3,4-diol

실험 절차

To the compound from Step 1 is added tosylmethyl isocyanide (1 eq.) in MeoH containing K2CO3 (1 eq.) and the mixture is heated to reflux until starting material is consumed. The solvent is removed in vacuo and the crude mixture purified by RP HPLC on a Phenominex column (250×20 mm) using a gradient of acetonitrile in water from 0 to 30% over 30 minutes at 10 mL/minute.