Serinol → HCID 11951515, compound

HRID 1454448Notes

Reaction equation

HRID 1454448 reaction equation
[Cl:1][C:2]1[C:3]2[CH:14]=[CH:13][C:12](=[O:15])[N:11]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=3)[C:4]=2[N:5]=[C:6](S(C)=O)[N:7]=1.[NH2:26][CH:27]([CH2:30][OH:31])[CH2:28][OH:29]>ClCCl.CN(C=O)C>[Cl:1][C:2]1[C:3]2[CH:14]=[CH:13][C:12](=[O:15])[N:11]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=3)[C:4]=2[N:5]=[C:6]([NH:26][CH:27]([CH2:30][OH:31])[CH2:28][OH:29])[N:7]=1

Participants

5

Reactant 2

HCID 68294SerinolHCID 11951347HCID 11951347, compound

Product 1

HCID 11951515HCID 11951515, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-Chloro-2-methylsulfinyl-8-(4-trifluoromethyl-phenyl)-8H-pyrido[2,3-d]pyrimidin-7-one (0.29 g, 0.75 mmol) in dichloromethane (30 mL) was mixed with a solution of serinol (0.075 g, 0.82 mmol) in DMF (0.75 mL). The resultant mixture was stirred at room temperature for 1 hour before concentrated under vacuum. Flash chromatography (EtOAc:Hexane, 3:1) then provided the title compound (0.14 g, 45%): MS (ES) m/z 415 (M+H)+; 1H-NMR(CDCl3) δ 2.25 (s, br, 2H), 3.66 (m, br, 5H), 6.15 (m, br, 1H), 6.55 (d, J=9.2 Hz, 1H), 7.36 (m, 2H), 7.81 (d, J=8.1 Hz, 2H), 7.92 (d, J=9.2 Hz, 1H).

Workup

  1. concentrationbefore concentrated under vacuum

Sources & evidence

ORD record
ord-38d3dbdc0a604d64b25685250d634ac0
Source dataset
uspto-grants-2009_01
Patent number
US07479558B2

Reaction notes

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