Methanol → HCID 59184870, compound

HRID 426285Notes

Reaction equation

[C:1]([O:5][C:6](=[O:28])[N:7]([C:19]1[CH:24]=[C:23]([CH3:25])[CH:22]=[C:21]([C:26]#[N:27])[CH:20]=1)[C:8]1[C:13]([CH:14]([CH3:16])[CH3:15])=[C:12](Cl)[N:11]=[C:10](Cl)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:29][O-:30].[Na+].[CH3:32][OH:33]>>[C:1]([O:5][C:6](=[O:28])[N:7]([C:19]1[CH:24]=[C:23]([CH3:25])[CH:22]=[C:21]([C:26]#[N:27])[CH:20]=1)[C:8]1[C:13]([CH:14]([CH3:16])[CH3:15])=[C:12]([O:30][CH3:29])[N:11]=[C:10]([O:33][CH3:32])[N:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 3

HCID 887Methanol

HCID 10942334Sodium Methoxide

HCID 59184801HCID 59184801, compound

Product 1

HCID 59184870HCID 59184870, compound

Conditions

Temperature: 75 °C

Procedure

(3-Cyano-5-methyl-phenyl)-(2,6-dichloro-5-isopropyl-pyrimidin-4-yl)-carbamic acid tert-butyl ester (469 mg, 1.113 mmol) was dissolved in methanol (4 mL) at room temperature. Sodium methoxide solution (25% in methanol, 1.18 g, 5.56 mmol) was added and the reaction was heated at 75° C. After 4 hours, the reaction was stopped by the evaporation of solvents. The crude material was purified via flash chromatography on silica gel (eluent: ethyl acetate in hexanes) to yield (3-Cyano-5-methyl-phenyl)-(2,6-dimethoxy-5-isopropyl-pyrimidin-4-yl)-carbamic acid tert-butyl ester (336.8 mg, 0.816 mmol). 1H (CDCl3): δ=7.36 (s, 1H), 7.31 (s, 1H), 7.20 (s, 1H), 4.02 (s, 3H), 3.92 (s, 3H), 3.01 (m, 1H), 2.32 (s, 3H), 1.41 (s, 9H), 1.20-1.10 (m, 6H) ppm.

Workup

customthe reaction was stopped by the evaporation of solvents
customThe crude material was purified via flash chromatography on silica gel (eluent: ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-5c8c8f03d13849309124a00b444ba218
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106064B2

Reaction notes

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