Potassium Phosphate, Tribasic → N-(4-(2,6-dimethylphenylthio)pyridin-2-yl)-4-methylthiazol-2-amine

HRID 910988Notes

Reaction equation

HRID 910988 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH2:7])[S:5][CH:6]=1.Cl[C:9]1[CH:14]=[C:13]([S:15][C:16]2[C:21]([CH3:22])=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:23])[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>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]>[CH3:22][C:21]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:23])[C:16]=1[S:15][C:13]1[CH:12]=[CH:11][N:10]=[C:9]([NH:7][C:4]2[S:5][CH:6]=[C:2]([CH3:1])[N:3]=2)[CH:14]=1

Participants

6

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 866347342-Chloro-4-(2,6-dimethylphenylthio)pyridine

Product 1

HCID 24826588N-(4-(2,6-dimethylphenylthio)pyridin-2-yl)-4-methylthiazol-2-amineYield 48%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

Using the method of Example 3, Step B, 4-methylthiazol-2-amine (0.274 g, 2.40 mmol), 2-chloro-4-(2,6-dimethylphenylthio)pyridine (0.600 g, 2.40 mmol), potassium phosphate (0.561 g, 2.64 mmol), Pd2(dba)3 (0.110 g, 0.120 mmol), and 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (0.070 g, 0.120 mmol) were reacted to provide N-(4-(2,6-dimethylphenylthio)pyridin-2-yl)-4-methylthiazol-2-amine (0.375 g, 48% yield). 1H NMR (d6-DMSO) δ 11.01 (s, 1H), 8.03 (d, 1H), 7.31-7.40 (m, 3H), 6.57 (s, 1H), 6.50 (s, 1H), 6.41 (d, 1H), 2.40 (s, 6H), 2.20 (s, 3H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-e83ee38f576f4ea0a7ed5b5c7a41cf77
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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