Acetonitrile → HCID 135899298, compound

HRID 2100465Notes

Reaction equation

HRID 2100465 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][OH:12])=[CH:5][CH:4]=1.Cl[C:14]1[NH:19][C:18]2[N:20]=[CH:21][CH:22]=[CH:23][C:17]=2[C:16](=[O:24])[N:15]=1.CC([O-])(C)C.[K+].CC#N>CS(C)=O.C(O)(C(F)(F)F)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][O:12][C:14]2[NH:15][C:16](=[O:24])[C:17]3[CH:23]=[CH:22][CH:21]=[N:20][C:18]=3[N:19]=2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 794063-(4-Methoxyphenyl)-1-propanolHCID 23665647Potassium tert-butoxideHCID 178517828HCID 178517828, compound

Product 1

HCID 135899298HCID 135899298, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
120 °C

Procedure

In a screw-capped glass tube, 3-(4-methoxyphenyl)-1-propanol ([5406-18-8], 137 mg, 0.826 mmol) was added to a mixture of 2-chloropyrido[2,3-d]pyrimidin-4(1H)-one ([93049-38-8], 50 mg, 0.28 mmol) and KOtBu (62 mg, 0.55 mmol) in DMSO (2 ml). The mixture was heated (3 days, 120° C.) and the title compound was isolated from the product mixture by reversed-phase, preparative HPLC (Agilent Zorbax XdB C18 column, solvent gradient 5-95% CH3CN in 0.1% TFA(aq) over 7 min, flow rate 30 ml/min). MS: m/e=310.5 [M−H−], 1H NMR (d6-DMSO): δ 2.02 (dd, 2H), 3.36 (d, 2H), 3.71 (s, 3H), 4.42 (d, 2H), 6.86 (d, 2H), 7.15 (d, 2H), 7.36 (dd, 1H), 8.38 (d, 1H), 8.79 (d, 1H).

Sources & evidence

ORD record
ord-068c881b690c45889f35cf091ec9256e
Source dataset
uspto-grants-2009_08
Patent number
US07572801B2

Reaction notes

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