tert-Butyl carbamate → tert-Butyl (5-(pyrimidin-5-yloxy)pyridin-3-yl)carbamate

HRID 1045814Notes

Reaction equation

HRID 1045814 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:8][C:9]2[CH:10]=[N:11][CH:12]=[N:13][CH:14]=2)[CH:5]=[N:6][CH:7]=1.[C:15](=[O:22])([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[NH2:16].CC(C)([O-])C.[Na+].C(P(C(C)(C)C)C1C=CC=CC=1C1C(C(C)C)=CC(C(C)C)=CC=1C(C)C)(C)(C)C>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C(Cl)(Cl)Cl.[Pd].[Pd]>[N:11]1[CH:10]=[C:9]([O:8][C:4]2[CH:3]=[C:2]([NH:16][C:15](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH:7]=[N:6][CH:5]=2)[CH:14]=[N:13][CH:12]=1

Participants

7

Reactant 4

HCID 77922tert-Butyl carbamateHCID 11618717Di-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphaneHCID 23676156Sodium t-butoxideHCID 510379325-((5-Bromopyridin-3-yl)oxy)pyrimidine

Product 1

HCID 58349145tert-Butyl (5-(pyrimidin-5-yloxy)pyridin-3-yl)carbamateYield 100%

Reagents, catalysts & solvents 2

HCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)CatalystHCID 1140TolueneSolvent

Procedure

Compound 5 (1.0 g, 4.0 mmol, 1.0 eq), tert-Butyl carbamate (560 mg, 4.78 mmol, 1.20 eq), tris(dibenzylideneacetone) dipalladium-chloroform adduct (120 mg, 0.116 mmol, 0.0300 eq), sodium tert-butoxide (530 mg, 5.52 mmol, 1.40 eq), and 2-Di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl (180 mg, 0.424 mmol, 0.0900 eq) stirred in toluene (15 mL) at rt overnight. The mixture was filtered through celite and washed with 5% MeOH in CH2Cl2. The filtrate was collected and concentrated in vacuo to afford 1.1 g (100%) of the title compound as an orange solid: 1H NMR (400 MHz, DMSO-d6) δ 9.79 (s, 1H), 9.05 (s, 1H), 8.72 (s, 2H), 8.45 (d, J=1.7 Hz, 1H), 8.10 (t, J=2.5 Hz, 1H), 7.69 (s, 1H), 1.45 (s, 9H); ES-MS [M+1]+: 289.1.

Workup

  1. filtrationThe mixture was filtered through celite
  2. washwashed with 5% MeOH in CH2Cl2
  3. customThe filtrate was collected
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-00c9530691ef40e79b612811f91bc504
Source dataset
uspto-grants-2013_10
Patent number
US08569308B2

Reaction notes

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