1,3-Dioxolane, 2-(bromomethyl)- → 4-(1,3-Dioxolan-2-ylmethoxy)-6-methoxy-2-pyrimidinamine

HRID 1284411

Reaction equation

HRID 1284411 reaction equation
[NH2:1][C:2]1[NH:7][C:6](=[O:8])[CH:5]=[C:4](C)[N:3]=1.C[C:11](C)([O-:13])C.[K+].Br[CH2:17][CH:18]1[O:22][CH2:21][CH2:20][O:19]1>CN(C)C=O>[O:19]1[CH2:20][CH2:21][O:22][CH:18]1[CH2:17][O:8][C:6]1[CH:5]=[C:4]([O:13][CH3:11])[N:3]=[C:2]([NH2:1])[N:7]=1

Participants

5

Reactant 3

HCID 780681,3-Dioxolane, 2-(bromomethyl)-HCID 23665647Potassium tert-butoxideHCID 1354020552-Amino-6-methylpyrimidin-4-one

Product 1

HCID 202515004-(1,3-Dioxolan-2-ylmethoxy)-6-methoxy-2-pyrimidinamineYield 16.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 8.5 g (0.060 mol) 2-amino-6-methyl-4-pyrimidinone in 45 mL anhydrous dimethylformamide (DMF) was treated with 6.7 g (0.060 mol) potassium t-butoxide then stirred for 10 minutes at ambient temperature. Subsequently, 7.6 mL (0.073 mol) of 2-bromomethyl-1,3-dioxolane was added and the mixture heated to 120° for 3 hours. The DMF was then evaporated under reduced pressure and the residue partitioned between water and ethyl acetate. The aqueous phase was extracted with two additional portions of ethyl acetate then the combined organic phase was washed with water, brine, then dried (MgSO4) and evaporated to an oil. Chromatography on silica gel with 10% ethyl acetate/CH2Cl2 as the eluant afforded 2.3 g of the title compound as a viscous oil. NMR (CDCl3): δ 3.9 (s, 3H), 4.0 (m, 4H), 4.3 (d, J=4 Hz, 2H), 5.15 (NH, br), 5.27 (t, J=4 Hz, 1H), 5.55 (s, 1H) ppm.

Workup

  1. temperaturethe mixture heated to 120° for 3 hours
  2. customThe DMF was then evaporated under reduced pressure
  3. customthe residue partitioned between water and ethyl acetate
  4. extractionThe aqueous phase was extracted with two additional portions of ethyl acetate
  5. washthe combined organic phase was washed with water, brine
  6. dry with materialdried (MgSO4)
  7. customevaporated to an oil

Sources & evidence

ORD record
ord-1e0c63b1eb114db292b9c1ff6a270ba1
Source dataset
uspto-grants-1986_01
Patent number
US04563211

Linked notes

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