Sodium Iodide → 2-Amino-4-chloro-6-pyrimidylacetonitrile
Reaction equation
C(OC(=O)C[C:8]1[C:9]([Cl:17])=[N:10][C:11]([NH2:16])=[N:12][C:13]=1[C:14]#N)(C)(C)C.[I-].[Na+].Cl[Si](C)(C)C.[C:26](#[N:28])C>>[NH2:16][C:11]1[N:10]=[C:9]([Cl:17])[CH:8]=[C:13]([CH2:14][C:26]#[N:28])[N:12]=1Participants
Conditions
- Temperature
- 40 °C
Procedure
2-amino-4-chloro-6-cyano-pyrimidylacetate-t-butyl ester (100 g, 372.5 mmol) was suspended in dry acetonitrile (1.2 l) containing sodium iodide (55.84 g, 372.5 mmol) and warmed to 40° C. until the mixture became homogeneous. Then chlorotrimethylsilane (200 ml) was added and the orange suspension was heated at reflux. After 1 hour, TLC analysis (elute with 1:1 ethyl acetate/hexanes) indicated a complete reaction and the reaction was filtered and the filtrate was concentrated. The residue was diluted with ethyl acetate and washed with water and sodium bicarbonate solution and dried with magnesium sulfate. The crude product was slurried in activated carbon, filtered and concentrated to give 38.46 g of a green solid. This was again dissolved in ethyl acetate and passed through a 4-inch pad of silica gel and then concentrated to give the desired subject as a green solid, m.p. 110°-115° C. NMR (200 mHz) D6-acetone δ 6.8 (s, 1 H), 6.8-6.6 (bs, 1 H), 3.95 (s, 2 H).
Workup
- temperaturethe orange suspension was heated
- temperatureat reflux
- washTLC analysis (elute with 1:1 ethyl acetate/hexanes)
- customa complete reaction
- filtrationthe reaction was filtered
- concentrationthe filtrate was concentrated
- additionThe residue was diluted with ethyl acetate
- washwashed with water and sodium bicarbonate solution
- dry with materialdried with magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-84325f7a73134de28703c120f054c11c
- Source dataset
- uspto-grants-1989_07
- Patent number
- US04844727
Reaction notes
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