3-Phenoxy 1-propanol → 6-Chloro-2-(3-phenoxy-propoxy)-3H-pyrido[2,3-d]pyrimidin-4-one

HRID 2100519Notes

Reaction equation

HRID 2100519 reaction equation
Cl[C:2]1[NH:3][C:4](=[O:13])[C:5]2[CH:11]=[C:10]([Cl:12])[CH:9]=[N:8][C:6]=2[N:7]=1.[O:14]([CH2:21][CH2:22][CH2:23][OH:24])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CC([O-])(C)C.[K+]>CS(C)=O>[Cl:12][C:10]1[CH:9]=[N:8][C:6]2[N:7]=[C:2]([O:24][CH2:23][CH2:22][CH2:21][O:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[NH:3][C:4](=[O:13])[C:5]=2[CH:11]=1

Participants

5

Reactant 3

HCID 803193-Phenoxy 1-propanolHCID 23665647Potassium tert-butoxideHCID 1363459252,6-dichloro-3H-pyrido[2,3-d]pyrimidin-4-one

Product 1

HCID 1358992106-Chloro-2-(3-phenoxy-propoxy)-3H-pyrido[2,3-d]pyrimidin-4-oneYield 2.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 2,6-dichloro-3H-pyrido[2,3-d]pyrimidin-4-one (60 mg, crude), 3-phenoxy-1-propanol [6180-61-6] (127 mg, 0.84 mmol), and KOtBu (62 mg, 0.55 mmol) in DMSO (1 ml) was heated in a microwave oven to 180° C. for 15 min. After filtration, the title compound (2.3 mg, 6.9 Amok; 2.5%, MS: m/e=330.3 [M−H−]) was obtained from the reaction mixture by preparative, reverse-phase HPLC (Agilent Zorbax XdB C18 column, solvent gradient 5-95% CH3CN in 0.1% TFA(aq) over 7 min, flow rate 30 ml/min).

Workup

  1. filtrationAfter filtration

Sources & evidence

ORD record
ord-b2da52114835456fbb46468f7b96ffe5
Source dataset
uspto-grants-2009_08
Patent number
US07572801B2

Reaction notes

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