Acetic Acid → 2-Amino-4-methoxy-6-pyrimidylacetonitrile

2-amino-4-chloro-6-pyrimidylacetonitrile (31.6 g, 204.6 mmol) was dissolved in methanol (500 ml) and then sodium methoxide in methanol (46.8 ml, 204.6 mmol) was added at 25° C. The resultant dark solution was heated at reflux for 1 hour and after this time TLC indicated complete reaction. The reaction was cooled and acidified to pH 6 with acetic acid and the mixture was filtered. The filtrated was concentrated and the residue was taken up in ethyl acetate and washed with water and brine and dried with magnesium sulfate. The brown solid was chromatographed on silica gel using 1:1 ethyl acetate/hexane as eluent to furnish two fractions. Fraction A furnished 6.9 g of pure subject as a yellow solid, m.p. 117°-118° C. Fraction B furnished 4.23 g of impure subject as a pink solid, m.p. 95°-98° C. NMR (fraction A) (90 mHz) D6-acetone δ 6.2-5.9 (bs, 2 H), 6.1 (s, 1 H), 3.9 (s, 3 H), 3.7 (s, 2 H). EXAMPLE 4

1. temperatureThe resultant dark solution was heated
2. temperatureat reflux for 1 hour
3. customreaction
4. temperatureThe reaction was cooled
5. filtrationthe mixture was filtered
6. concentrationThe filtrated was concentrated
7. washwashed with water and brine
8. dry with materialdried with magnesium sulfate
9. customThe brown solid was chromatographed on silica gel using 1:1 ethyl acetate/hexane as eluent
10. customto furnish two fractions
11. customFraction B furnished 4.23 g of impure

ORD record

ord-d17b892463d94e939c94549524d184d7

Source dataset

uspto-grants-1989_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04844727