Sodium Azide → 2-(azidomethyl)-3H,4H,5H,7H,8H-pyrano[4,3-d]pyrimidin-4-one

To a solution of 2-chloromethyl-3,5,7,8-tetrahydro-pyrano[4,3-d]pyrimidin-4-one (20.6 g, 103 mmol) in acetone (513 mL) was added an aqueous solution of sodium azide (7.01 g, 108 mmol in 32 mL water). Reaction was stirred at room temperature for 36 h. Mixture was split into three equal volumes and each was diluted with dichloromethane (500 mL) and brine was added (100 mL) and the layers were separated. The aqueous fractions were combined and extracted with dichloromethane (5×100 mL). The combined organic layers were concentrated in vacuo. The resulting residue was taken up in dichloromethane (200 mL) and evaporated to dryness three times to yield 19.25 g of a yellow-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.59 (t, J=5.56 Hz, 2H) 3.85 (t, J=5.56 Hz, 2H) 4.28 (s, 2H) 4.36 (s, 2H) 12.58 (br. s., 1H)

1. customReaction
2. customMixture was split into three equal volumes
3. additioneach was diluted with dichloromethane (500 mL) and brine
4. additionwas added (100 mL)
5. customthe layers were separated
6. extractionextracted with dichloromethane (5×100 mL)
7. concentrationThe combined organic layers were concentrated in vacuo
8. customevaporated to dryness three times

ORD record

ord-ac40acc9e4c3402183b1527ae760e922

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09181266B2