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

HRID 1524846Notes

Reaction equation

HRID 1524846 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-5171e4c52f22489d8c65ce3ab147ca0e
Source dataset
uspto-grants-2015_07
Patent number
US09079916B2

Reaction notes

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