Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | tert-Butyl acetate | HCID 10908 | — |
| Reactant | Lithium Hexamethyldisilazide | HCID 2733832 | — |
| Reactant | HCID 22648121 | HCID 22648121 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 22648007 | HCID 22648007 | — |
Reaction Steps
To a −78° C. solution of LiHMDS (4.1 mL) in 3 mL of THF was added t-butylacetate (0.6 mL). After stirring for 10 min, 1.0 g of 5-(bromomethyl)-4-chloro-6-(2,4-difluorophenyl)-2-(methylthio)pyrimidine (COMPOUND VV-3) in 4 mL of THF was added dropwise. The mixture was stirred at −78° C. for 1.5 h, then warmed to −50° C. The reaction mixture was recooled to −78° C. and 3 mL of methanol was added. The solution stirred for 24 h at rt. The crude mixture was purified by flash chromatography, eluting with 2% diethyl ether/hexanes. Mass spectrum m/z (ESI) 401.5 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06809199B2 |
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| Source dataset | uspto-grants-2004_10 |
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| ORD ID | ord-385412c2a46044e5bf6ee848c1615286 |
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| Source note | uspto-grants-2004_10 |
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