N,N-Dimethylaniline → HCID 86667838, compound

HRID 1913239Notes

Reaction equation

HRID 1913239 reaction equation
[C:1]([O:5][C:6]([CH:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[C:18](O)[N:17]3[N:21]=[CH:22][CH:23]=[C:16]3[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C)C1C=CC=CC=1.O=P(Cl)(Cl)[Cl:35]>>[C:1]([O:5][C:6]([CH:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[C:18]([Cl:35])[N:17]3[N:21]=[CH:22][CH:23]=[C:16]3[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 178450659HCID 178450659, compound

Product 1

HCID 86667838HCID 86667838, compoundYield 32%

Procedure

4-(7-Hydroxy-pyrazolo[1,5-a]pyrimidin-5-yl)-cyclohexanecarboxylic acid t-butyl ester (Int-7b, 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 was reduced in vacuo and cooled to 0° C. in ice bath. The reaction was then quenched with sat. NaHCO3(aq) and extracted with DCM (100 mL×3). The combined organics were dried with Na2SO4 and the solvent was removed in vacuo. The resulting oil was purified via silica gel column on 20% to 100% ethyl acetate in hexanes gradient to yield the title compound (2.5 g, 32% over three steps). LC-MS: 336 [M+H].

Workup

  1. temperaturecooled to 0° C. in ice bath
  2. customThe reaction was then quenched with sat. NaHCO3(aq)
  3. extractionextracted with DCM (100 mL×3)
  4. dry with materialThe combined organics were dried with Na2SO4
  5. customthe solvent was 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-ee5e98cbe26c48f2ac8dda5255b6bcc2
Source dataset
uspto-grants-2013_12
Patent number
US08609675B2

Reaction notes

Loading…