Sodium Carbonate → 4-(6-Methoxypyridin-3-yl)-5-methylpyrimidin-2-amine

HRID 2069378Notes

Reaction equation

HRID 2069378 reaction equation
Cl[C:2]1[C:7]([CH3:8])=[CH:6][N:5]=[C:4]([NH2:9])[N:3]=1.[CH3:10][O:11][C:12]1[N:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.C([O-])([O-])=O.[Na+].[Na+]>>[CH3:10][O:11][C:12]1[N:17]=[CH:16][C:15]([C:2]2[C:7]([CH3:8])=[CH:6][N:5]=[C:4]([NH2:9])[N:3]=2)=[CH:14][CH:13]=1

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 5886284-Chloro-5-methylpyrimidin-2-amineHCID 2734368(6-Methoxypyridin-3-yl)boronic acid

Product 1

HCID 578561844-(6-Methoxypyridin-3-yl)-5-methylpyrimidin-2-amineYield 43%

Conditions

Temperature
120 °C

Procedure

To 4-chloro-5-methylpyrimidin-2-amine (250 mg, 1.74 mmol), tetrakistriphenylphosphine palladium (0) (100 mg, 0.087 mmol) and 6-methoxypyridin-3-ylboronic acid (398 mg, 2.60 mmol), 1,2-DME (6 mL) and Na2CO3 (1.74 mL, 2 M, 3.47 mmol) were added and heated to 120° C. in a microwave reactor for 30 minutes. The reaction mixture was filtered using acetonitrile and the filtrate was dried over anhydrous Na2SO4 and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel to yield 4-(6-methoxypyridin-3-yl)-5-methylpyrimidin-2-amine (160 mg, 43%). ESI-MS m/z calc. 216.10, found 217.5 (M+1)+. Retention time 0.52 minutes.

Workup

  1. filtrationThe reaction mixture was filtered
  2. dry with materialthe filtrate was dried over anhydrous Na2SO4
  3. customevaporated under reduced pressure
  4. customThe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-edeca402091e41fc9fd38d715f13315f
Source dataset
uspto-grants-2012_10
Patent number
US08299099B2

Reaction notes

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