Reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8]O)=[CH:4][N:3]=1.C1(C)C=CC=CC=1.C1C=CC(OP(OC2C=CC=CC=2)([N:26]=[N+:27]=[N-:28])=O)=CC=1.N12CCCN=C1CCCCC2>O.C(Cl)Cl>[N:26]([CH2:8][C:5]1[CH:4]=[N:3][C:2]([CH3:1])=[N:7][CH:6]=1)=[N+:27]=[N-:28]Participants
7
Conditions
- Temperature
- 0 °C
Procedure
A solution of (2-methylpyrimidin-5-yl)methanol (0.82 g, 6.6 mmol) in toluene (30 mL, 300 mmol) and methylene chloride (40 mL, 600 mmol) at 0° C. was treated with diphenylphosphonic azide (2.8 mL, 13 mmol) followed by 1,8-diazabicyclo[5.4.0]undec-7-ene (2.0 mL, 13 mmol) and stirred for 2 h at 0° C. After being further stirred at rt for 16 h, the reaction mixture was diluted with water (50 mL) and DCM (50 mL). The organic layer was separated and washed with brine, dried (Mg2SO4), filtered, and concentration. The residue was purified by column to give the product as a colorless oil.
Workup
- stirringAfter being further stirred at rt for 16 h
- customThe organic layer was separated
- washwashed with brine
- dry with materialdried (Mg2SO4)
- filtrationfiltered
- concentrationconcentration
- customThe residue was purified by column
Sources & evidence
- ORD record
- ord-dc6dc165eeaa4449bbfc8b23cb514a24
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09133122B2
Linked notes
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