Sodium Carbonate → HCID 58456111, compound

HRID 410415Notes

Reaction equation

HRID 410415 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([NH:10][C:11]2[CH:16]=[C:15](B3OC(C)(C)C(C)(C)O3)[CH:14]=[C:13]([CH3:26])[CH:12]=2)[N:5]=1)([CH3:3])[CH3:2].Br[C:28]1[S:32][CH:31]=[N:30][CH:29]=1.C(=O)([O-])[O-].[Na+].[Na+]>CC1CCCO1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[CH:1]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([NH:10][C:11]2[CH:16]=[C:15]([C:28]3[S:32][CH:31]=[N:30][CH:29]=3)[CH:14]=[C:13]([CH3:26])[CH:12]=2)[N:5]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 5460595-BromothiazoleHCID 67249155HCID 67249155, compound

Product 1

HCID 58456111HCID 58456111, compoundYield 83.1%

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 73012-MethyltetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-isopropyl-N-(3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidin-2-amine (500 mg, 1.42 mmol) in 2-methyl tetrahydrofuran (7.1 mL) were added 5-bromothiazole (318 mg, 1.84 mmol), PdCl2(dppf)-CH2Cl2 (58 mg, 0.07 mmol), and aqueous sodium carbonate (2 M, 1.42 mL). The reaction was sealed and purged with N2 for 5 minutes. The reaction was stirred at 80° C. for 16 h and cooled to room temperature. Water was added and extracted with EtOAc (3×). The combined organic layers were dried over magnesium sulfate, concentrated in vacuo, and purified by flash chromatography to give 4-isopropyl-N-(3-methyl-5-(thiazol-5-yl)phenyl)pyrimidin-2-amine (366 mg, 1.18 mmol, 83% yield) as an off-white solid. MS ESI: [M+H]+ m/z 311.1. 1H NMR (500 MHz, DMSO-d6) δ 9.59 (s, 1H), 9.05 (s, 1H), 8.38 (d, J=4.7, 1H), 8.19 (s, 1H), 8.13 (s, 1H), 7.51 (s, 1H), 7.11 (s, 1H), 6.77 (d, 5.1, 1H), 2.87 (m, 1H), 2.30 (s, 3H), 1.25 (d, J=6.8, 6H).

Workup

  1. customThe reaction was sealed
  2. custompurged with N2 for 5 minutes
  3. temperaturecooled to room temperature
  4. additionWater was added
  5. extractionextracted with EtOAc (3×)
  6. dry with materialThe combined organic layers were dried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. custompurified by flash chromatography

Sources & evidence

ORD record
ord-71775d19b19f4dc78d53d8ce2c19f137
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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