2-溴甲基-1,3-二氧戊烷 → 4-(1,3-Dioxolan-2-ylmethoxy)-6-methoxy-2-pyrimidinamine

HRID 1284411

反应方程式

HRID 1284411 反应方程式
[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

参与物

5

反应物 3

HCID 780682-溴甲基-1,3-二氧戊烷HCID 23665647叔丁醇钾HCID 1354020552-氨基-4-羟基-6-甲基嘧啶

产物 1

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

试剂、催化剂与溶剂 1

HCID 6228N,N-二甲基甲酰胺溶剂

实验过程

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.

后处理

  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

来源与证据

ORD记录
ord-1e0c63b1eb114db292b9c1ff6a270ba1
来源数据集
uspto-grants-1986_01
专利号
US04563211

关联笔记

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