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

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	Tosylmethyl isocyanide	HCID 161915	—
Reactant	4-Chloro-7-(3,4-dihydroxy-5-hydroxymethyl-3-methyl-tetrahydrofuran-2-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbaldehyde	HCID 21040838	—
Product	2-(4-Chloro-5-oxazol-5-yl-pyrrolo[2,3-d]pyrimidin-7-yl)-5-hydroxymethyl-3-methyl-tetrahydro-furan-3,4-diol	HCID 86623589	—

Reaction Steps

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.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07629320B2
Source dataset	uspto-grants-2009_12
ORD ID	ord-7b25b6896d034eaa96b3ebad32f0adda
Source note	uspto-grants-2009_12