2-Methanesulfonyl-4-methyl-8H-pyrido[2,3-d]pyrimidin-7-one → 4-Methyl-2-[4-(4-naphthalen-1-yl-piperazin-1-yl)-butoxy]-8H-pyrido[2,3-d]pyrimidin-7-one

HRID 1373628Notes

Reaction equation

HRID 1373628 reaction equation
CS([C:5]1[N:6]=[C:7]([CH3:16])[C:8]2[CH:14]=[CH:13][C:12](=[O:15])[NH:11][C:9]=2[N:10]=1)(=O)=O.[C:17]1([N:27]2[CH2:32][CH2:31][N:30]([CH2:33][CH2:34][CH2:35][CH2:36][OH:37])[CH2:29][CH2:28]2)[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1.CC(C)([O-])C.[Na+]>O1CCOCC1>[CH3:16][C:7]1[C:8]2[CH:14]=[CH:13][C:12](=[O:15])[NH:11][C:9]=2[N:10]=[C:5]([O:37][CH2:36][CH2:35][CH2:34][CH2:33][N:30]2[CH2:31][CH2:32][N:27]([C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:20]=[CH:19][CH:18]=3)[CH2:28][CH2:29]2)[N:6]=1

Participants

5

Reactant 3

HCID 210732772-Methanesulfonyl-4-methyl-8H-pyrido[2,3-d]pyrimidin-7-oneHCID 210733524-(4-Naphthalen-1-yl-piperazin-1-yl)-butan-1-olHCID 23676156Sodium t-butoxide

Product 1

HCID 210734034-Methyl-2-[4-(4-naphthalen-1-yl-piperazin-1-yl)-butoxy]-8H-pyrido[2,3-d]pyrimidin-7-oneYield 38%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-Methanesulfonyl-4-methyl-8H-pyrido[2,3-d]pyrimidin-7-one (300 mg, 1.245 mmol, U.S. Pat. No. 6,498,163), 4-(4-naphthalen-1-yl-piperazin-1-yl)-butan-1-ol (392 mg, 1.379 mmol) and sodium t-butoxide (362 mg, 3.76 mmol) were combined in a vial. Dioxane (10 mL) was added and the solution was stirred for 1 h. The reaction mixture was concentrated and then partitioned between ethyl acetate and water. The organic layer was washed with water, dried over Na2SO4, filtered and concentrated. Purification by liquid chromatography (MPLC, gradient of 100% CH2Cl2 to 100% of 100:8:1 CH2Cl2:EtOH:NH4OH solution) gave the title compound as a solid (220 mg, 0.485 mmol, 38%). MS: APCI: M+1: 444.2 (Exact Mass: 443.23).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompartitioned between ethyl acetate and water
  3. washThe organic layer was washed with water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by liquid chromatography (MPLC, gradient of 100% CH2Cl2 to 100% of 100:8:1 CH2Cl2:EtOH:NH4OH solution)

Sources & evidence

ORD record
ord-60bef06f94414191a0abb0e9b3c28e37
Source dataset
uspto-grants-2007_01
Patent number
US07160888B2

Reaction notes

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