N,N-Dimethylaniline → HCID 86664779, compound

HRID 2047016Notes

Reaction equation

HRID 2047016 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:16]=[C:15](O)[N:14]3[N:18]=[CH:19][CH:20]=[C:13]3[N:12]=2)[CH2:7][CH2:6]1)=[O:4].CN(C)C1C=CC=CC=1.O=P(Cl)(Cl)[Cl:32]>>[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:16]=[C:15]([Cl:32])[N:14]3[N:18]=[CH:19][CH:20]=[C:13]3[N:12]=2)[CH2:7][CH2:6]1)=[O:4]

Participants

4

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 178497545HCID 178497545, compound

Product 1

HCID 86664779HCID 86664779, compoundYield 32%

Procedure

4-(7-Hydroxy-pyrazolo[1,5-a]pyrimidin-5-yl)-cyclohexanecarboxylic acid methyl ester (10.6 g), N,N-dimethylaniline (15.0 ml) and POCl3 (120 mL) were mixed and stirred at room temperature for 18 hours. The solution is reduced in vacuo and cooled to 0° C. in ice bath. The reaction is then quenched with sat. NaHCO3(aq) and extracted with DCM (100 mL×3). The combined organics are dried with Na2SO4 and the solvent removed in vacuo. The resulting oil was purified via silica gel column on 20% to 100% ethyl acetate in hexanes gradient to yield the titled compound (2.5 g, 32% over three steps). LC-MS: 294 [M+H].

Workup

  1. temperaturecooled to 0° C. in ice bath
  2. customThe reaction is then quenched with sat. NaHCO3(aq)
  3. extractionextracted with DCM (100 mL×3)
  4. dry with materialThe combined organics are dried with Na2SO4
  5. customthe solvent removed in vacuo
  6. customThe resulting oil was purified via silica gel column on 20% to 100% ethyl acetate in hexanes gradient

Sources & evidence

ORD record
ord-b7bba07f21aa460baa54fadb364e3fe0
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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