Acetic Acid → 5-(2-Isopropyl-4-methoxy-5-thiazol-2-yl-phenoxy)-pyrimidine-2,4-diamine
Reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([O:9][C:10]2[C:11]([CH:21]([CH3:23])[CH3:22])=[CH:12][C:13]([O:19][CH3:20])=[C:14]([CH:18]=2)[C:15]([NH2:17])=[S:16])=[CH:4][N:3]=1.C([O-])(O)=O.[Na+].[CH3:29][C:30](O)=O>C(OC(OCC)CBr)C.CC1C=CC(S(O)(=O)=O)=CC=1>[CH:21]([C:11]1[CH:12]=[C:13]([O:19][CH3:20])[C:14]([C:15]2[S:16][CH:29]=[CH:30][N:17]=2)=[CH:18][C:10]=1[O:9][C:5]1[C:6]([NH2:8])=[N:7][C:2]([NH2:1])=[N:3][CH:4]=1)([CH3:23])[CH3:22]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 110 °C
Procedure
To a solution of 5-(2,4-Diamino-pyrimidin-5-yloxy)-4-isopropyl-2-methoxy-thiobenzamide (0.23 g, 0.69 mmol) in HOAc (5 ml) was added bromoactaldehyde diethylacetal (0.18 g, 0.9 mmol) and TsOH (5 mg) as a catalyst. The reaction mixture was heated at 110° C. for 16 hrs and basified with sat. NaHCO3 solution. The aqueous solution was extracted into methylene chloride. The combined organic extract was dried over Na2SO4, filtered and concentrated. Flash chromatography on silica (5% MeOH in methylene chloride with 1% NH4OH) gave 5-(2-Isopropyl-4-methoxy-5-thiazol-2-yl-phenoxy)-pyrimidine-2,4-diamine (0.070 g, 28%) as a yellow solid. (M+H)=358.
Workup
- extractionThe aqueous solution was extracted into methylene chloride
- extractionThe combined organic extract
- dry with materialwas dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-03feaca1d98340bfab66ba748bc3d1ff
- Source dataset
- uspto-grants-2011_08
- Patent number
- US08008313B2
Reaction notes
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