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

HRID 1284411

反応式

HRID 1284411 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1e0c63b1eb114db292b9c1ff6a270ba1
出典データセット
uspto-grants-1986_01
特許番号
US04563211

関連ノート

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