Diethyl Ether → HCID 178516393, compound

HRID 241079Notes

Reaction equation

HRID 241079 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([OH:8])[CH:3]=1.[NH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)C(C)C)(C)C.C(OCC)C>COCCOCCOC>[C:10]1([NH:9][C:2]2[N:7]=[CH:6][N:5]=[C:4]([OH:8])[CH:3]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6115AnilineHCID 81531DiisopropylethylamineHCID 178516195HCID 178516195, compound

Product 1

HCID 178516393HCID 178516393, compoundYield 35.5%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

6-Chloropyrimidin-4-ol (500 mg, 3.85 mmol), aniline (420 μL, 4.62 mmol) and N,N-diisopropylethylamine (1 mL) in diethylene glycol dimethyl ether (5 mL) was heated to 120° C. and stirred for 8 h. The mixture was cooled to room temperature then diluted with actone:diethyl ether solution (1:1, 15 ml) to give a precipitate. The solid collected by filtration and washed with acetone then dried to afford 6-(phenylamino)pyrimidin-4-ol (255 mg, 35.5%). MS (EI) for C10H9N3O: 188.2 (MH+).

Workup

  1. additionthen diluted with actone
  2. filtrationThe solid collected by filtration
  3. washwashed with acetone
  4. customthen dried

Sources & evidence

ORD record
ord-1e154a5ef4df4ca9958f68214a0019e5
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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