Chloroacetaldehyde → 7-Deazaguanine

Temperature

65 °C

To a mixture of 2,4-diamino-6-hydroxypyrimidine (20.0 g, 159 mmol) and NaOAc (26.0 g, 317 mmol) in H2O (300 mL) at 65° C. was added a solution of chloroacetaldehyde (22.0 mL, 50% in H2O, 173 mmol) in H2O (22 mL) dropwise for 90 min. The mixture was stirred at 65° C. for an additional 2 h and cooled to room temperature. The reaction mixture was concentrated in vacuo to one third of its original volume and stored at 4° C. for 16 h. The light pink precipitates were filtered, washed with an ice cold H2O (5 mL), and dried under high vacuum for 16 h. The precipitates were placed in Soxhlet extractor and refluxed with methanol (200 mL) for 24 h. The methanol was concentrated to give 13.3 g (56%) of 2-amino-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one as a light pink solid.

1. temperaturecooled to room temperature
2. concentrationThe reaction mixture was concentrated in vacuo to one third of its original volume
3. waitstored at 4° C. for 16 h
4. customThe light pink precipitates
5. filtrationwere filtered
6. washwashed with an ice cold H2O (5 mL)
7. customdried under high vacuum for 16 h
8. temperaturerefluxed with methanol (200 mL) for 24 h
9. concentrationThe methanol was concentrated

ORD record

ord-28923e8ab0cf4f2382f37ed6be972a1a

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08354532B2