Acetic Acid → (2,4-Dihydroxypyrido[3,2-d]pyrimidin-6-yl)methyl acetate

Temperatur

100 °C

Into a 5000-mL 4-necked round-bottom flask was placed a solution of 6-methylpyrido[3,2-d]pyrimidine-2,4(1H,3H)-dione 2 (120 g, 677.97 mmol, 1.00 equiv) in acetic acid (2400 mL). This was followed by the addition of m-CBPA (608 g, 3.51 mol, 5.18 equiv) in several batches. The resulting solution was stirred overnight at 100° C. The resulting mixture was cooled and concentrated under vacuum. The residue was washed with 2×1500 mL of ether and 2×500 mL of DCM, then it was dissolved in HOAc (1200 mL) and acetic anhydride (500 mL). The resulting solution was stirred for 0.5 h at 110° C. The reaction mixture was cooled and filtered. The filtrate was concentrated under vacuum. The residue was washed with 2×500 ml of ether and dried. This resulted in 80 g (50%) of (2,4-dioxo-1,2,3,4-tetrahydropyrido[3,2-d]pyrimidin-6-yl)methyl acetate 3 as a brown solid.

1. customInto a 5000-mL 4-necked round-bottom flask was placed
2. additionThis was followed by the addition of m-CBPA (608 g, 3.51 mol, 5.18 equiv) in several batches
3. temperatureThe resulting mixture was cooled
4. concentrationconcentrated under vacuum
5. washThe residue was washed with 2×1500 mL of ether and 2×500 mL of DCM
6. dissolutionit was dissolved in HOAc (1200 mL)
7. stirringThe resulting solution was stirred for 0.5 h at 110° C
8. temperatureThe reaction mixture was cooled
9. filtrationfiltered
10. concentrationThe filtrate was concentrated under vacuum
11. washThe residue was washed with 2×500 ml of ether
12. customdried
13. customThis resulted in 80 g (50%) of (2,4-dioxo-1,2,3,4-tetrahydropyrido[3,2-d]pyrimidin-6-yl)methyl acetate 3 as a brown solid

ORD-Eintrag

ord-ed818dbae2084e8ab7d6e2d167ea35b4

Quelldatensatz

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08563540B2