Cesium carbonate → t-Butyl(4-{[2-(methylthio)pyrimidin-4-yl]oxy}-1-naphthyl)carbamate

HRID 1171270Notes

Reaction equation

HRID 1171270 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:4][CH:3]=1.I[C:21]1[CH:26]=[CH:25][N:24]=[C:23]([S:27][CH3:28])[N:22]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C(Cl)Cl>[CH3:28][S:27][C:23]1[N:24]=[C:25]([O:1][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[CH:4][CH:3]=2)[CH:26]=[CH:21][N:22]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 38589014-Iodo-2-(methylthio)pyrimidineHCID 10923237tert-Butyl (4-hydroxynaphthalen-1-yl)carbamate

Product 1

HCID 59553280t-Butyl(4-{[2-(methylthio)pyrimidin-4-yl]oxy}-1-naphthyl)carbamateYield 56.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of t-butyl (4-hydroxy-1-naphthyl)carbamate (5.0 g, 19.3 mmol), 4-iodo-2-methylthiopyrimidine (4.86 g, 19.3 mmol) and cesium carbonate (7.52 g, 23.1 mmol) in DMF (25 ml) is heated at 70° C. for 20 h. The resulting mixture is diluted with CH2Cl2 (50 ml), washed with water (25 ml×3), dried over Na2SO4 and concentrated. This residue is dissolved in minimum volume of EtOAc at 70° C. and then hexane (20 ml) is added. The resulting solution is left at room temperature overnight, filtered and washed with hexane to obtain t-butyl (4-{[2-(methylthio)pyrimidin-4-yl]oxy}-1-naphthyl)carbamate as a pink solid (4.2 g); Mp: 173-174° C.; 1H NMR (300 MHz, CDCl3) δ 1.56 (s, 9 H), 2.30 (s, 3H), 6.45 (d, J=5.7 Hz, 1H), 6.86 (s, 1H), 7.27 (d, J=8.1Hz, 1H), 7.47-7.60 (m, 2H), 7.87-7.94 (m, 3H), 8.32 (d, J=5.7 Hz, 1H); MS: 384 (M+1).

Workup

  1. washwashed with water (25 ml×3)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. dissolutionThis residue is dissolved in minimum volume of EtOAc at 70° C.
  5. additionhexane (20 ml) is added
  6. filtrationfiltered
  7. washwashed with hexane

Sources & evidence

ORD record
ord-0d9e310ab2004d719725e1b346a05288
Source dataset
uspto-grants-2010_11
Patent number
US07829560B2

Reaction notes

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