Triethylamine → 2-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butoxy)pyrido[2,3-d]pyrimidin-7(8H)-one

HRID 1373624Notes

Reaction equation

HRID 1373624 reaction equation
[O:1]=[C:2]1[NH:17][C:6]2[N:7]=[C:8]([O:11][CH2:12][CH2:13][CH2:14][CH:15]=O)[N:9]=[CH:10][C:5]=2[CH:4]=[CH:3]1.Cl.[Cl:19][C:20]1[C:25]([Cl:26])=[CH:24][CH:23]=[CH:22][C:21]=1[N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1.CCN(CC)CC.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClC(Cl)C>[Cl:19][C:20]1[C:25]([Cl:26])=[CH:24][CH:23]=[CH:22][C:21]=1[N:27]1[CH2:32][CH2:31][N:30]([CH2:15][CH2:14][CH2:13][CH2:12][O:11][C:8]2[N:9]=[CH:10][C:5]3[CH:4]=[CH:3][C:2](=[O:1])[NH:17][C:6]=3[N:7]=2)[CH2:29][CH2:28]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 116303721-(2,3-Dichlorophenyl)piperazine hydrochlorideHCID 21073381HCID 21073381, compound

Product 1

HCID 210732162-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butoxy)pyrido[2,3-d]pyrimidin-7(8H)-oneYield 83%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a suspension of 4-(7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-yloxy)-butyraldehyde (235 mg, 1.01 mmol) in dichloroethane (5 mL) was added 1-(2,3-dichloro-phenyl)-piperazine hydrochloride (270 mg, 1.01 mmol) followed by Et3N (0.28 mL, 2.0 mmol, 2 equiv). After 10 min at RT, NaBH(OAc)3 (297 mg, 1.4 mmol) was added as a powder. The reaction was stirred for 2 h at room temperature and quenched with saturated NaHCO3 and H2O. The mixture was extracted with EtOAc (with a little MeOH to help dissolve the solids). The organic layer was washed with brine and concentrated. Purification by liquid chromatography (5% MeOH/CH2Cl2 with 1% NH4OH) gave the title compound as a white solid (375 mg, 0.836 mmol, 83%). MS: APCI: M+1: 448.1 (Exact Mass: 447.12).

Workup

  1. customquenched with saturated NaHCO3 and H2O
  2. extractionThe mixture was extracted with EtOAc (with a little MeOH
  3. dissolutionto help dissolve the solids)
  4. washThe organic layer was washed with brine
  5. concentrationconcentrated
  6. customPurification by liquid chromatography (5% MeOH/CH2Cl2 with 1% NH4OH)

Sources & evidence

ORD record
ord-701aab5c6eb24245b22153f27b9fe477
Source dataset
uspto-grants-2007_01
Patent number
US07160888B2

Reaction notes

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