Sodium Carbonate → Tert-butyl 3-(2-amino-5-methylpyrimidin-4-yl)benzoate

HRID 1524840Notes

Reaction equation

HRID 1524840 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:18]=[C:19](B(O)O)[CH:20]=[CH:21][CH:22]=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:21]2[CH:22]=[C:17]([CH:18]=[CH:19][CH:20]=2)[C:15]([O:14][C:10]([CH3:12])([CH3:13])[CH3:11])=[O:16])[C:7]([CH3:8])=[CH:6][N:5]=1

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 5886284-Chloro-5-methylpyrimidin-2-amineHCID 2773299(3-((Tert-butoxy)carbonyl)phenyl)boronic acid

Product 1

HCID 57856193Tert-butyl 3-(2-amino-5-methylpyrimidin-4-yl)benzoateYield 50%

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 3-(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 3-(2-amino-5-methylpyrimidin-4-yl)benzoate (148 mg, 50%). ESI-MS m/z calc. 285.1. Found 286.5 (M+1)+. Retention time 1.33 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-105a5bde0814453683e09e7171acde6c
Source dataset
uspto-grants-2015_07
Patent number
US09079916B2

Reaction notes

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