Triethylamine → N-[(2-amino-1,3-thiazol-4-yl)methyl]-6-chloro-5-fluoro-2-methyl-4-pyrimidinamine

HRID 1366489Notes

Reaction equation

HRID 1366489 reaction equation
Cl[C:2]1[C:7]([F:8])=[C:6]([Cl:9])[N:5]=[C:4]([CH3:10])[N:3]=1.C[NH:12][CH2:13][C:14]1[N:15]=[C:16]([NH2:19])[S:17][CH:18]=1.C(N(CC)CC)C>C1COCC1>[NH2:19][C:16]1[S:17][CH:18]=[C:14]([CH2:13][NH:12][C:2]2[C:7]([F:8])=[C:6]([Cl:9])[N:5]=[C:4]([CH3:10])[N:3]=2)[N:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 137310334,6-Dichloro-5-fluoro-2-methylpyrimidineHCID 189398714-((Methylamino)methyl)thiazol-2-amine

Product 1

HCID 86636959N-[(2-amino-1,3-thiazol-4-yl)methyl]-6-chloro-5-fluoro-2-methyl-4-pyrimidinamineYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4,6-Dichloro-5-fluoro-2-methylpyrimidine (480 mg, 2.65 mmol) was dissolved in 20 mL of THF and stirred at room temperature. (4-[(Methylamino)methyl]-1,3-thiazol-2-amine (2.65 mmol, theoretical) was added, followed by triethylamine (400 μL, 2.92 mmol). The resulting reaction mixture was stirred overnight and evaporated. The residue was stirred in water and the solid precipitate was collected by filtration and was dried in vacuo to provide N-[(2-amino-1,3-thiazol-4-yl)methyl]-6-chloro-5-fluoro-2-methyl-4-pyrimidinamine (450 mg, 59%) that was used without further purification. LCMS: (M+H)+: 288.1.

Workup

  1. customThe resulting reaction mixture
  2. stirringwas stirred overnight
  3. customevaporated
  4. stirringThe residue was stirred in water
  5. filtrationthe solid precipitate was collected by filtration
  6. customwas dried in vacuo

Sources & evidence

ORD record
ord-e64767c8fdea4014a0fc9455e508827b
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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