Triphenylphosphine → 7-Hydroxy-1-methyl-2,3-dihydroimidazo[1,2-C]pyrimidin-5(1H)-one

HRID 873038Notes

Reaction equation

HRID 873038 reaction equation
O[CH2:2][CH2:3][N:4]([CH3:13])[C:5]1[NH:10][C:9](=[O:11])[NH:8][C:7](=[O:12])[CH:6]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1>[CH3:13][N:4]1[C:5]2[N:10]([C:9](=[O:11])[NH:8][C:7](=[O:12])[CH:6]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 867241596-((2-hydroxyethyl)(methyl)amino)pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 596353557-Hydroxy-1-methyl-2,3-dihydroimidazo[1,2-C]pyrimidin-5(1H)-oneYield 99.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 6-((2-hydroxyethyl)(methyl)amino)pyrimidine-2,4(1H,3H)-dione (0.463 g, 2.5 mmol) in tetrahydrofuran (310 ml) at rt was added Ph3P (1.967 g, 7.50 mmol), then DIAD (1.458 ml, 7.50 mmol) was added dropwise. The reaction mixture was stirred at rt for 3 h, and concentrated. The residue was partitioned between ethyl ether and water. The aqueous phase was separated, washed with ethyl ether again, and then concentrated to afford the title compound as a light-yellow solid (0.414 g, 99% yield).

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between ethyl ether and water
  3. customThe aqueous phase was separated
  4. washwashed with ethyl ether again
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e2de2b01afab4e919be4aacf0f8542af
Source dataset
uspto-grants-2015_03
Patent number
US08975400B2

Reaction notes

Loading…