Methanol → HCID 20626966, compound
Reaction equation
[F:1][C:2]1[CH:24]=[CH:23][C:5]([O:6][C:7]2[C:20](=[O:21])[N:19]([CH3:22])[C:10]3[N:11]=[C:12](S(C)(=O)=O)[N:13]=[CH:14][C:9]=3[CH:8]=2)=[CH:4][CH:3]=1.[CH2:25]([N:27]([CH2:38][CH3:39])[CH2:28][CH2:29][O:30][C:31]1[CH:37]=[CH:36][C:34]([NH2:35])=[CH:33][CH:32]=1)[CH3:26].CO>CN1CCCC1=O>[CH2:38]([N:27]([CH2:25][CH3:26])[CH2:28][CH2:29][O:30][C:31]1[CH:32]=[CH:33][C:34]([NH:35][C:12]2[N:13]=[CH:14][C:9]3[CH:8]=[C:7]([O:6][C:5]4[CH:23]=[CH:24][C:2]([F:1])=[CH:3][CH:4]=4)[C:20](=[O:21])[N:19]([CH3:22])[C:10]=3[N:11]=2)=[CH:36][CH:37]=1)[CH3:39]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 110 °C
Procedure
A mixture of 6-(4-fluorophenoxy)-8-methyl-2-(methylsulfonyl) pyrido[2,3-d]pyrimidin-7(8H)-one (see Example 8—Step A–B, 0.35 g, 1 mmol) and 4-(2-diethylaminoethoxy) aniline (0.625 g, 3 mmol) in 0.5 mL 1-methyl-2-pyrrolidinone was stirred at 110° C. for 12 hours and then cooled to room temperature. Methanol (2 mL) was added and the suspension was stirred for 30 minutes. Filtration and washing of the precipitate thoroughly with methanol followed by drying provided the free amine. This was suspended in ethyl acetate (1–2 mL), hydrochloric acid in ether (1M, 1.2 eq) was added and the reaction was stirred for 30 minutes. Isolation of the solid via filtration and drying provided 0.085 g of the hydrochloride salt (Mass spec. M+1=478, MP=245.2–246.1° C.).
Workup
- temperaturecooled to room temperature
- stirringthe suspension was stirred for 30 minutes
- filtrationFiltration
- washwashing of the precipitate thoroughly with methanol
- customby drying
Sources & evidence
- ORD record
- ord-58a799cf899040dfa156abd137ddc23c
- Source dataset
- uspto-grants-2007_01
- Patent number
- US07169794B2
Reaction notes
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