Methyl 4-aminobenzoate → HCID 89456982, compound

HRID 1485654Notes

Reaction equation

HRID 1485654 reaction equation
C[Si]([N-:5][Si](C)(C)C)(C)C.[Na+].Cl[C:12]1[CH:17]=[C:16]([Cl:18])[N:15]=[C:14]([S:19][CH3:20])[N:13]=1.[NH2:21][C:22]1C=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=1>C1COCC1>[Cl:18][C:16]1[N:15]=[C:14]([S:19][CH3:20])[N:13]=[C:12]([NH:5][C:22]2[CH:23]=[CH:24][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:30][N:21]=2)[CH:17]=1

Participants

5

Reactant 3

HCID 12082Methyl 4-aminobenzoateHCID 805314,6-Dichloro-2-(methylthio)pyrimidineHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 89456982HCID 89456982, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

NaHMDS (65.7 mL, 1M in THF) was added into the solution of 4,6-dichloro-2-(methylthio)pyrimidine (6.4 g) and methyl 4-aminobenzoate (5 g) in THF (200 mL). The reaction was stirred at room temperature for 16 hours, before being quenched by water. The aqueous layer was extracted with EtOAc (3×200 mL). The combined organic phase was dried over MgSO4 and concentrated under vacuum to give the crude product, methyl 6-(6-chloro-2-(methylthio)pyrimidin-4-ylamino)nicotinate, which was used in the next step without purification.

Workup

  1. custombefore being quenched by water
  2. extractionThe aqueous layer was extracted with EtOAc (3×200 mL)
  3. dry with materialThe combined organic phase was dried over MgSO4
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-b2b69c265312427ea12be282e19f7c0b
Source dataset
uspto-grants-2016_08
Patent number
US09422311B2

Reaction notes

Loading…