4,6-Dichloro-2-(methylthio)pyrimidine → HCID 86679314, compound

HRID 469272Notes

Reaction equation

HRID 469272 reaction equation
C[Si]([N-][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]1[CH:34]=[CH:33][C:25]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[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:21][C:22]2[CH:34]=[CH:33][C:25]([C:26]([O:28][C:29]([CH3:30])([CH3:31])[CH3:32])=[O:27])=[CH:24][CH:23]=2)[CH:17]=1

Participants

5

Reactant 3

HCID 805314,6-Dichloro-2-(methylthio)pyrimidineHCID 233272Benzoic acid, 4-amino-, 1,1-dimethylethyl esterHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 86679314HCID 86679314, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

NaHMDS (41 mL, 1M in THF) was added into the solution of 4,6-dichloro-2-(methylthio)pyrimidine (4 g) and tert-butyl 4-aminobenzoate (3.96 g) in THF (200 mL). The reaction was stirred at room temperature for 16 hours, before being quenched by water (100 mL). The aqueous layer was extracted with EtOAc (3×100 mL)). The combined organic phase was dried over MgSO4 and concentrated under vacuum to give tert-butyl 4-(6-chloro-2-(methylthio)pyrimidin-4-ylamino)benzoate which will be used without purification.

Workup

  1. custombefore being quenched by water (100 mL)
  2. extractionThe aqueous layer was extracted with EtOAc (3×100 mL))
  3. dry with materialThe combined organic phase was dried over MgSO4
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-94838e8f8c174116bb4bf9deac42ff21
Source dataset
uspto-grants-2014_01
Patent number
US08629150B2

Reaction notes

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