Water → 2-(Aminomethyl)-7,8-dihydro-3H-pyrano[4,3-D]pyrimidin-4(5H)-one

HRID 713387Notes

Reaction equation

HRID 713387 reaction equation
[N:1]([CH2:4][C:5]1[NH:6][C:7](=[O:15])[C:8]2[CH2:14][O:13][CH2:12][CH2:11][C:9]=2[N:10]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1>[NH2:1][CH2:4][C:5]1[NH:6][C:7](=[O:15])[C:8]2[CH2:14][O:13][CH2:12][CH2:11][C:9]=2[N:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 1366272502-(azidomethyl)-3H,4H,5H,7H,8H-pyrano[4,3-d]pyrimidin-4-one

Product 1

HCID 1357418942-(Aminomethyl)-7,8-dihydro-3H-pyrano[4,3-D]pyrimidin-4(5H)-oneYield 94.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(azidomethyl)-7,8-dihydro-3H-pyrano[4,3-d]pyrimidin-4(5H)-one (19 g, 92 mmol) in THF (945 mL) at 35° C. was added triphenylphosphine (26.5 g, 101 mmol). Gas evolution was noted immediately and after approximately 40 minutes a fine precipitate formed. The reaction was allowed to stir for 1.5 h then 18.17 mL water was added. After an addition 2 h the reaction mixture was cooled to room temperature, filtered twice, concentrated to approximately ⅓ of the original volume and filtered once more. The solid material was washed with THF to yield a total of 15.82 g of the title compound. 1H NMR (400 MHz, MeOD) δ ppm 2.66 (t, J=5.56 Hz, 2H) 3.76 (s, 2H) 3.94 (t, J=5.56 Hz, 2H) 4.49 (s, 2H)

Workup

  1. customa fine precipitate formed
  2. additionAfter an addition 2 h the reaction mixture
  3. filtrationfiltered twice
  4. concentrationconcentrated to approximately ⅓ of the original volume
  5. filtrationfiltered once more
  6. washThe solid material was washed with THF

Sources & evidence

ORD record
ord-7d08dc9a490d422a9b1424fe5b79207f
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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