1,8-Diazabicyclo(5.4.0)undec-7-ene → 5-(Azidomethyl)-2-methylpyrimidine

HRID 657748Notes

Reaction equation

[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8]O)=[CH:4][N:3]=1.C1C=CC(OP(OC2C=CC=CC=2)([N:19]=[N+:20]=[N-:21])=O)=CC=1.N12CCCN=C1CCCCC2>C1(C)C=CC=CC=1.C(Cl)Cl.O>[N:19]([CH2:8][C:5]1[CH:4]=[N:3][C:2]([CH3:1])=[N:7][CH:6]=1)=[N+:20]=[N-:21]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of (2-methylpyrimidin-5-yl)methanol (0.82 g, 6.6 mmol) in toluene (30 mL) and methylene chloride (40 mL) 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 at 0° C. for 2 h. After being further stirred at rt for 16 h, the reaction mixture was diluted with water (50 mL) and methylene chloride (50 mL). The organic layer was separated and washed with brine, dried (Mg2SO4), filtered, and concentration. The residue was purified by silica gel column to yield 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 silica gel column
customto yield a colorless oil

Sources & evidence

ORD record: ord-3d3d0b07d9b84da49fe303d46f429500
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08076345B2

Reaction notes

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