Water → 6-[(4-fluorophenyl)thio]-8-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one
Reaction equation
CNC1C([CH:9]=[S:10])=CN=C(C)N=1.COC(=O)C[S:16][C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1.N1CCC[N:27]2[CH2:31][CH2:32][CH2:33][N:34]=[C:26]12.O.[CH3:36][N:37]1C[CH2:40][CH2:39][C:38]1=[O:42]>>[F:23][C:20]1[CH:21]=[CH:22][C:17]([S:16][C:39]2[C:38](=[O:42])[N:37]([CH3:36])[C:31]3[N:27]=[C:26]([S:10][CH3:9])[N:34]=[CH:33][C:32]=3[CH:40]=2)=[CH:18][CH:19]=1Participants
6
Reactant 5
Product 1
Conditions
- Temperature
- 120 °C
Procedure
To a mixture of 4-methylamino-2-methylthiopyrimidine-5-carboxaldehyde (0.55 g, 3 mmol) and methyl(4-fluorophenylthio)acetate (prepared as in Example 5 using 4-fluorothiophenol, 0.65 g, 3.3 mmol) in 25 mL of 1-methyl-2-pyrrolidinone was added 1,3,4,6,7,8-hexahydro-2H-pyrimido(1,2-a)pyrimidine polymer bound resin base (Aldrich, 200 mg). The reaction mixture was heated to 120° C. After 12 hours it was cooled to room temperature and added to water (50 mL). The aqueous mixture was extracted with ethyl acetate (75 mL) yielding a organic solution which was washed with water (2×, 50 mL) and dried (brine, Na2SO4). Evaporation of the solvent yielded 0.95 g of the sulfide (mass spec. M+1=334).
Workup
- temperatureAfter 12 hours it was cooled to room temperature
- extractionThe aqueous mixture was extracted with ethyl acetate (75 mL)
- customyielding a organic solution which
- washwas washed with water (2×, 50 mL)
- dry with materialdried (brine, Na2SO4)
- customEvaporation of the solvent
Sources & evidence
- ORD record
- ord-3c452487053c4fc09e2bf987fe0346b5
- Source dataset
- uspto-grants-2008_11
- Patent number
- US07449581B2
Reaction notes
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