Potassium Carbonate → Pyrimidine, 2-ethynyl-4-methoxy- (9CI)

HRID 1500742Notes

Reaction equation

HRID 1500742 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][N:24]=[C:23]([C:27]#[C:28][Si](C)(C)C)[N:22]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.C(O)(=O)C>[C:27]([C:23]1[N:22]=[C:21]([O:20][CH3:19])[CH:26]=[CH:25][N:24]=1)#[CH:28]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2724141Tetrabutylammonium FluorideHCID 10375706HCID 10375706, compound

Product 1

HCID 10011938Pyrimidine, 2-ethynyl-4-methoxy- (9CI)Yield 85%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Tetrabutylammonium fluoride (0.97 mL of a 1M solution in tetrahydrofuran, 0.97 mmol) was added to a stirred solution of 4-methoxy-2-[(trimethylsilyl)ethynyl]pyrimidine (Preparation 1a, 0.20 g, 0.97 mmol) in tetrahydrofuran (1.4 mL) and acetic acid (56 pt) at room temperature. After 5 minutes, 10% aqueous potassium carbonate solution was added to the reaction mixture and the mixture was extracted with dichloromethane. The organic layer was separated, dried (MgSO4) and evaporated. Purification of the residue by flash chromatography (dichloromethane) gave the title compound (0.11 g, 85%) as a pale orange solid.

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customPurification of the residue by flash chromatography (dichloromethane)

Sources & evidence

ORD record
ord-9ab85e8e7cdb4923a58090db0032f309
Source dataset
uspto-grants-2015_12
Patent number
US09206183B2

Reaction notes

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