4,6-Dichloro-2-(methylthio)pyrimidine → Ethyl 6-(6-chloro-2-(methylthio)pyrimidin-4-ylamino)nicotinate

HRID 469273

Reaction equation

HRID 469273 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([S:9][CH3:10])[N:3]=1.[NH2:11][C:12]1[CH:22]=[CH:21][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:14][N:13]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>C1COCC1.O>[Cl:8][C:6]1[N:5]=[C:4]([S:9][CH3:10])[N:3]=[C:2]([NH:11][C:12]2[CH:22]=[CH:21][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:14][N:13]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 805314,6-Dichloro-2-(methylthio)pyrimidineHCID 235927Ethyl 6-AminonicotinateHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 86679315Ethyl 6-(6-chloro-2-(methylthio)pyrimidin-4-ylamino)nicotinate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4,6-dichloro-2-(methylthio)pyrimidine (1 g), ethyl 6-aminonicotinate (0.85 g) and NaHMDS (10.3 mL, 1M in THF) in THF (50 mL) was stirred at room temperature for 16 hours. The mixture was diluted with water and extracted with EtOAc (2×150 mL). The organic layers were combined, washed with brine (50 mL), dried over MgSO4 and concentrated to give ethyl 6-(6-chloro-2-(methylthio)pyrimidin-4-ylamino)nicotinate which was used as was.

Workup

  1. extractionextracted with EtOAc (2×150 mL)
  2. washwashed with brine (50 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-93d8f17e7b9343648392cf65a432290e
Source dataset
uspto-grants-2014_01
Patent number
US08629150B2

Linked notes

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