Cesium carbonate → Tert-butyl 6-(methoxymethyl)pyrimidin-4-ylcarbamate

HRID 1241401Notes

Reaction equation

HRID 1241401 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH2:8][O:9][CH3:10])[N:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH3:17][C:18]1(C)[C:44]2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=C[C:19]1=2.C([NH:63][C:64](=[O:66])[O-:65])(C)(C)C>O1CCOCC1.O.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.[Pd].[Pd]>[CH3:10][O:9][CH2:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:63][C:64](=[O:66])[O:65][C:18]([CH3:44])([CH3:19])[CH3:17])[CH:7]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 143061714-Chloro-6-(methoxymethyl)pyrimidineHCID 21252905Tert-butylcarbamate

Product 1

HCID 21934671Tert-butyl 6-(methoxymethyl)pyrimidin-4-ylcarbamate

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-chloro-6-(methoxymethyl)pyrimidine (768 mg, 4.84 mmole) in dry dioxane (10 mL) was added Cs2CO3 (2.37 g, 7.26 mmole), Xanthphos (84 mg, 0.15 mmole), Pd2(dba)3 (44 mg, 0.05 mmole), and tert-butylcarbamate (681 mg, 5.81 mmole) then the mixture was heated to reflux. After 3 hours, the mixture was cooled to room temperature, diluted with H2O, and extracted with CH2Cl2 (3×). The combined organic layers were dried (MgSO4), filtered, and concentrated. Flash column chromatography (35% EtOAc/hexanes) gave the title compound as a pale yellow solid. 1H-NMR (500 MHz, CDCl3) δ 8.74 (s, 1H), 8.04 (s, 1H), 8.00 (bs, 1H), 4.51 (s, 2H), 3.51 (s, 3H), 1.55 (s, 9H).

Workup

  1. temperaturethe mixture was heated to reflux
  2. extractionextracted with CH2Cl2 (3×)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-094a03491c6d47d49c0b03c1f6d3f794
Source dataset
uspto-grants-2006_10
Patent number
US07115597B2

Reaction notes

Loading…