Ammonium Chloride → t-Butyl [3-(4,6-dimethoxypyrimidin-2-ylmethyl)-2-pyridyl]carbamate

HRID 743979Notes

Reaction equation

C([Li])CCC.[CH3:6][C:7]1[C:8]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[N:9][CH:10]=[CH:11][CH:12]=1.[CH3:21][O:22][C:23]1[CH:28]=[C:27]([O:29][CH3:30])[N:26]=[C:25](S(C)(=O)=O)[N:24]=1.[Cl-].[NH4+]>CCCCCC.O1CCCC1>[CH3:21][O:22][C:23]1[CH:28]=[C:27]([O:29][CH3:30])[N:26]=[C:25]([CH2:6][C:7]2[C:8]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[N:9][CH:10]=[CH:11][CH:12]=2)[N:24]=1

Participants

Conditions

Temperature: -70 °C

Procedure

n-Butyllithium (19.2 ml of a 2.5M solution in hexane) was added dropwise to a stirred suspension of the product of stage (a) above (5.0 g) in dry tetrahydrofuran (100 ml) under nitrogen at -70° C. The mixture was stirred at -70° C. for 20 minutes and then at 5° C. for 3 hours. It was then cooled to -70° C. and treated with 4,6-dimethoxy-2-methylsulfonylpyrimidine (5.42 g), and the mixture was stirred at -70° C. for 1 hour, then at room temperature overnight. Saturated ammonium chloride solution (500 ml) was added, and the mixture was extracted with ethyl acetate (2×100 ml). The combined extracts were washed with saturated sodium chloride solution (50 ml), dried and evaporated to give an orange oil which was triturated with hexane to give 5.35 g of the desired product as a pale yellow solid, mp 89°-92° C.

Workup

waitat 5° C. for 3 hours
temperatureIt was then cooled to -70° C.
stirringthe mixture was stirred at -70° C. for 1 hour
customat room temperature
customovernight
extractionthe mixture was extracted with ethyl acetate (2×100 ml)
washThe combined extracts were washed with saturated sodium chloride solution (50 ml)
customdried
customevaporated
customto give an orange oil which
customwas triturated with hexane

Sources & evidence

ORD record: ord-a8e00f9564484d8e9c0b535adc77acb3
Source dataset: uspto-grants-1996_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05559081

Reaction notes

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