Sodium Carbonate → Tert-butyl 4-(2-amino-5-methylpyrimidin-4-yl)benzoate

HRID 2069375Notes

Reaction equation

HRID 2069375 reaction equation
Cl[C:2]1[C:7]([CH3:8])=[CH:6][N:5]=[C:4]([NH2:9])[N:3]=1.[C:10]([O:14][C:15]([C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1)=[O:16])([CH3:13])([CH3:12])[CH3:11].C([O-])([O-])=O.[Na+].[Na+]>>[NH2:9][C:4]1[N:3]=[C:2]([C:20]2[CH:21]=[CH:22][C:17]([C:15]([O:14][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:16])=[CH:18][CH:19]=2)[C:7]([CH3:8])=[CH:6][N:5]=1

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 5886284-Chloro-5-methylpyrimidin-2-amineHCID 2773301(4-((Tert-butoxy)carbonyl)phenyl)boronic acid

Product 1

HCID 57856165Tert-butyl 4-(2-amino-5-methylpyrimidin-4-yl)benzoateYield 50.2%

Conditions

Temperature
120 °C

Procedure

To 4-chloro-5-methylpyrimidin-2-amine (150 mg, 1.04 mmol), tetrakistriphenylphosphine Palladium (0) (60 mg, 0.052 mmol) and 4-(tert-butoxycarbonyl)phenylboronic acid (347 mg, 1.56 mmol), 1,2-DME (3 mL) and Na2CO3 (1.04 mL, 2 M, 2.08 mmol) were added and heated to 120° C. in a microwave reactor for 30 minutes. The reaction mixture was filtered using EtOAc 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 tert-butyl 4-(2-amino-5-methylpyrimidin-4-yl)benzoate (149 mg, 50%). ESI-MS m/z calc. 285.1, found 286.3 (M+1)+. Retention time 1.36 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-f120c665817348cc81c2e8b96e75a210
Source dataset
uspto-grants-2012_10
Patent number
US08299099B2

Reaction notes

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