Hydrochloric Acid → 2-[(6-chloro-2-methylpyrimidin-4-yl)amino]-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide

HRID 885631Notes

Reaction equation

HRID 885631 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:7]([NH:9][C:10]2[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:17])=[O:8])=[CH:5][N:6]=1.[Cl:18][C:19]1[CH:24]=[C:23](Cl)[N:22]=[C:21]([CH3:26])[N:20]=1.CC(C)([O-])C.[Na+].Cl>C1COCC1>[Cl:18][C:19]1[N:20]=[C:21]([CH3:26])[N:22]=[C:23]([NH:1][C:2]2[S:3][C:4]([C:7]([NH:9][C:10]3[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][C:11]=3[Cl:17])=[O:8])=[CH:5][N:6]=2)[CH:24]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 2349974,6-Dichloro-2-methylpyrimidineHCID 219116442-Amino-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamideHCID 23676156Sodium t-butoxide

Product 1

HCID 112694102-[(6-chloro-2-methylpyrimidin-4-yl)amino]-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamideYield 90.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirring solution of compound 5C (5.00 g, 18.67 mmol) and 4,6-dichloro-2-methylpyrimidine (3.65 g 22.4/mmol) in THF (65 mL) was added a 30% wt. solution of sodium t-butoxide in THF (21.1 g, 65.36 mmol) slowly with cooling to keep the temperature at 10-20° C. The mixture was stirred at room temperature for 1.5 h and cooled to 0-5° C. Hydrochloric acid, 2N (21.5 mL) was added slowly and the mixture stirred 1.75 h at 0-5° C. The solid was collected by vacuum filtration, washed with water (15 mL) and dried to give 6.63 g (86.4% yield) of compound 5D. 1H NMR (400 MHz, DMSO-d6) δ 2.23 (s, 3H), 2.58 (s, 3H), 6.94 (s, 1H), 7.18-7.34, (m, 2H, J=7.5), 7.34-7.46 (d, 1H, J=7.5), 8.31 (s, 1H), 10.02 (s, 1H), 12.25 (s, 1H).

Workup

  1. temperaturewith cooling
  2. customat 10-20° C
  3. temperaturecooled to 0-5° C
  4. stirringthe mixture stirred 1.75 h at 0-5° C
  5. filtrationThe solid was collected by vacuum filtration
  6. washwashed with water (15 mL)
  7. customdried

Sources & evidence

ORD record
ord-04ab9240122e4ed18b0890e12d0d0868
Source dataset
uspto-grants-2012_08
Patent number
US08242270B2

Reaction notes

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