3-Hydroxyazetidine hydrochloride → 6-(2-Fluoro-4-iodo-phenylamino)-5-(3-hydroxy-azetidine-1-carbonyl)-1,3-dimethyl-1H-pyrimidine-2,4-dione

Participants

Role	Name	HCID	Charge
Reactant	3-Hydroxyazetidine hydrochloride	HCID 2759290	—
Reactant	Phenyl 6-(2-fluoro-4-iodophenylamino)-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate	HCID 59259226	—
Product	6-(2-Fluoro-4-iodo-phenylamino)-5-(3-hydroxy-azetidine-1-carbonyl)-1,3-dimethyl-1H-pyrimidine-2,4-dione	HCID 25109219	52%

Reaction Steps

The title compound was synthesized from compound 2A and 3-hydroxyazetidine hydrochloride in 52% yield following a similar procedure described in the synthesis of Example 5. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.83 (s, 1H) 7.65 (d, J=9.85 Hz, 1H) 7.52 (d, J=9.60 Hz, 1H) 6.90-6.99 (m, 1H) 5.64 (d, J=5.31 Hz, 1H) 4.25-4.34 (m, 1H) 3.96-4.04 (m, 1H) 3.69-3.75 (m, 1H) 3.39-3.47 (m, 1H) 3.35 (s, 3H) 3.17-3.23 (m, 1H) 3.16 (s, 3H). [M+H] calc'd for C16H16FIN4O4, 475. found, 475.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07943626B2
Source dataset	uspto-grants-2011_05
ORD ID	ord-019906d3de5940d1b3a7a8d5ed2afa6c
Source note	uspto-grants-2011_05