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

反応式

[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

参加物

反応物 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

生成物 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

実験手順

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.