Potassium Phosphate, Tribasic → HCID 24825980, compound

HRID 910927Notes

Reaction equation

HRID 910927 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH2:7])[S:5][CH:6]=1.Cl[C:9]1[N:14]=[C:13]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:12]=[CH:11][N:10]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:9]2[N:14]=[C:13]([O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:12]=[CH:11][N:10]=2)[S:5][CH:6]=1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 741432-Amino-4-methylthiazoleHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 12679944Pyrimidine, 2-chloro-4-phenoxy-

Product 1

HCID 24825980HCID 24825980, compoundYield 10.3%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Using the method of Example 3, Step B, 4-methylthiazol-2-amine (7.66 mL, 3.07 mmol), 2-chloro-4-phenoxypyrimidine (0.697 g, 3.37 mmol), potassium phosphate (0.716 g, 3.37 mmol), Pd2(dba)3 (0.0702 g, 0.0766 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (0.0488 g, 0.0843 mmol) were reacted in toluene (8 mL) and water (3 mL) to afford 4-methyl-N-(4-phenoxypyrimidin-2-yl)thiazol-2-amine (0.09 g, 9.40% yield) as a light yellow solid. 1H NMR (CDCl3) δ 8.36 (d, 1H), 7.45 (m, 2H), 7.30 (m, 1H), 7.18 (m, 1H), 7.16 (m, 1H), 6.42 (d, 1H), 6.27 (bs, 1H), 2.30 (d, 3H); Mass spectrum (esi) m/z=385 (100) (M+H1).

Sources & evidence

ORD record
ord-bd636e7d762642e5acc14051737fb665
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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