Sodium Azide → HCID 58504435, compound

HRID 2367322Notes

Reaction equation

CS(O[CH2:6][C@H:7]1[O:12][CH2:11][C@@H:10]([CH3:13])[N:9]([C:14]2[CH:19]=[C:18]([Cl:20])[N:17]=[C:16]([NH2:21])[N:15]=2)[CH2:8]1)(=O)=O.[N-:22]=[N+:23]=[N-:24].[Na+]>CN(C=O)C.CCOC(C)=O>[N:22]([CH2:6][C@H:7]1[O:12][CH2:11][C@@H:10]([CH3:13])[N:9]([C:14]2[CH:19]=[C:18]([Cl:20])[N:17]=[C:16]([NH2:21])[N:15]=2)[CH2:8]1)=[N+:23]=[N-:24]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of crude [(2S,5R)-4-(2-amino-6-chloro-4-pyrimidinyl)-5-methyl-2-morpholinyl]methyl methanesulfonate (1.53 g, about 85% pure, 3.88 mmol) and sodium azide (0.382 g, 5.88 mmol) in DMF (75 mL) was stirred at 80° C. under nitrogen for 20.5 hours. Another portion of sodium azide (0.094 g, 1.45 mmol) was then added and stirring continued at 80° C. for an additional 6.5 hours. The mixture was then cooled, diluted with EtOAc (200 mL), washed with water (2×150 mL) and brine (1×150 mL), dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by flash chromatography (60 g SiO2, 1:1 hexanes/CH2Cl2 to 45:45:10 hexanes/CH2Cl2/CH3CN gradient) to give the title compound (890 mg) as a thick colorless oil. LC-MS (ES) m/z=284, 286 [M+H]+.

Workup

stirringstirring
waitcontinued at 80° C. for an additional 6.5 hours
temperatureThe mixture was then cooled
washwashed with water (2×150 mL) and brine (1×150 mL)
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by flash chromatography (60 g SiO2, 1:1 hexanes/CH2Cl2 to 45:45:10 hexanes/CH2Cl2/CH3CN gradient)

Sources & evidence

ORD record: ord-6e30e39ffb0544889e59a0f331a26da2
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697685B2

Reaction notes

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