Methanol → HCID 23434555, compound

HRID 270722Notes

Reaction equation

HRID 270722 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]([NH2:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.CO>CN1CCCC1=O>[CH2:25]([NH:32][C:12]1[N:13]=[CH:14][C:9]2[CH:8]=[C:7]([O:6][C:5]3[CH:23]=[CH:24][C:2]([F:1])=[CH:3][CH:4]=3)[C:20](=[O:21])[N:19]([CH3:22])[C:10]=2[N:11]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 7504BenzylamineHCID 52937846HCID 52937846, compound

Product 1

HCID 23434555HCID 23434555, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

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 made by replacing methyl 2-fluorophenoxyacetate with methyl 4-fluorophenoxyacetate-Steps A and B, 0.35 g, 1.0 mmol) and benzylamine (0.33 mL, 3 mmol) in 0.5 mL of 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 dissolved in ethyl acetate (1-2 mL) and hydrochloric acid in ether (1M, 1.5 eq) was added. Isolation of the solid via filtration and drying provided 0.317 g of the hydrochloride salt (Mass spec. M+1=377, MP=203.2-204° C.).

Workup

  1. temperaturecooled to room temperature
  2. stirringthe suspension was stirred for 30 minutes
  3. filtrationFiltration
  4. washwashing of the precipitate thoroughly with methanol
  5. customby drying

Sources & evidence

ORD record
ord-681e5a4b67744861a286e6edb29ec39f
Source dataset
uspto-grants-2008_11
Patent number
US07449581B2

Reaction notes

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