Hydrochloric Acid → 4-[2-(3-Nitrophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-phenyl-2-pyrimidinamine

HRID 1157541Notes

Reaction equation

HRID 1157541 reaction equation
CS([C:4]1[N:9]=[C:8]([C:10]2[C:11]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=3)=[N:12][N:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=23)[CH:7]=[CH:6][N:5]=1)=O.CCOC(C)=O.Cl.[NH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>>[N+:25]([C:21]1[CH:20]=[C:19]([C:11]2[C:10]([C:8]3[CH:7]=[CH:6][N:5]=[C:4]([NH:35][C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[N:9]=3)=[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][N:13]3[N:12]=2)[CH:24]=[CH:23][CH:22]=1)([O-:27])=[O:26]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 8857Ethyl AcetateHCID 595114013-[2-(Methylsulfinyl)-4-pyrimidinyl]-2-(3-nitrophenyl)pyrazolo[1,5-a]pyridine

Product 1

HCID 577372514-[2-(3-Nitrophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-phenyl-2-pyrimidinamineYield 52%

Conditions

Temperature
100 °C

Procedure

3-[2-(Methylsulfinyl)-4-pyrimidinyl]-2-(3-nitrophenyl)pyrazolo[1,5-a]pyridine (1.5 g, 3.9 mmol) was dissolved in aniline (5 mL). The dark mixture was heated at 100° C. for 5 h. The mixture was cooled and EtOAc (20 mL) and 1N HCl (10 mL) was added. The aqueous layer was extracted with EtOAc (20 mL) and the organic extracts combined, washed with 1N HCl, (15 mL), brine (10 mL), dried over MgSO4 and filtered. The organic solvent was removed in vacuo. The crude material was purified by silica gel chromatography (30-50% EtOAc/hexanes) to give the titled product (830 mg, 52% yield). 1H NMR (400 MHz, d6-DMSO) δ 6.58 (d, 1H, J=5.3 Hz), 6.98 (m, 1H), 7.05 (m, 1H), 7.19 (brs, 1H), 7.28-7.36 (m, 3H), 7.57-7.63 (m, 3H), 8.00 (m, 1H), 8.25-8.31 (m, 3H), 8.54 (m, 1H), 8.69 (m, 1H); ES-LC/MS: m/z (M+H)=409.

Workup

  1. temperatureThe mixture was cooled
  2. extractionThe aqueous layer was extracted with EtOAc (20 mL)
  3. washwashed with 1N HCl, (15 mL), brine (10 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customThe organic solvent was removed in vacuo
  7. customThe crude material was purified by silica gel chromatography (30-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-7df8f27032cf4e8b8bef591847ae7dab
Source dataset
uspto-grants-2010_10
Patent number
US07807673B2

Reaction notes

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