Methyl 7-methyl-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylate → 6-(Hydroxymethyl)-7-methyl-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one
Reaction equation
[CH3:1][C:2]1[C:11]([C:12](OC)=[O:13])=[N:10][C:9]2[NH:8][C:7](=[O:16])[CH2:6][S:5][C:4]=2[CH:3]=1>C1COCC1>[OH:13][CH2:12][C:11]1[C:2]([CH3:1])=[CH:3][C:4]2[S:5][CH2:6][C:7](=[O:16])[NH:8][C:9]=2[N:10]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -10 °C
Procedure
Methyl 7-methyl-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylate (54 mg, 0.195 mmol) was dissolved in THF (5 mL), cooled to −10° C. and treated with 1.0M LiH3BNMe2 (0.42 mL, 0.42 mmol). The reaction was maintained at −10° C. for 1 h and then quenched with 6N HCl. The reaction solution was diluted with EtOAc and water and the aqueous phase was extracted with EtOAc. The combined organic phases were dried (Na2SO4), filtered and concentrated. The crude product (30.3 mg) was used directly in the next step without further purification.
Workup
- additiontreated with 1.0M LiH3BNMe2 (0.42 mL, 0.42 mmol)
- temperatureThe reaction was maintained at −10° C. for 1 h
- customquenched with 6N HCl
- additionThe reaction solution was diluted with EtOAc and water
- extractionthe aqueous phase was extracted with EtOAc
- dry with materialThe combined organic phases were dried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated
- customThe crude product (30.3 mg) was used directly in the next step without further purification
Sources & evidence
- ORD record
- ord-44167344f08a401b8a7525f4f3482b23
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07691850B2
Reaction notes
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