2-Aminopyrimidine → HCID 68574319, compound

HRID 1949067Notes

Reaction equation

HRID 1949067 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([NH:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][CH3:21])[CH:6]=[CH:5]2.[NH2:22][C:23]1[N:28]=[CH:27][CH:26]=[CH:25][N:24]=1.[Na].CCSC(N(CC(C)C)CC(C)C)=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].O.O1CCOCC1>[CH3:21][O:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH2:13][NH:12][C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([NH:22][C:23]3[N:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[CH:3]=2)[N:8]=1

Participants

8

Reactant 4

HCID 79782-AminopyrimidineHCID 16181ButylateHCID 5360545SodiumHCID 68574436HCID 68574436, compound

Product 1

HCID 68574319HCID 68574319, compoundYield 36.4%

Reagents, catalysts & solvents 3

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

Procedure

A mixture of (6-bromo-quinolin-2-yl)-(2-methoxy-benzyl)-amine (see example 2, step A) (171.6 mg, 0.5 mmol), commercially available 2-amino-pyrimidine (95.1 mg, 1.0 mmol), tert.-butyl-XPhos (34 mg, 0.08 mmol), Pd2 dba3 (18.3 mg, 0.02 mmol), sodium tet.-butylate (52.9 mg, 0.55 mmol) and dioxane (3 ml) was heated in a sealed tube at 100° C. for 17 h. The reaction mixture was poured into water (20 ml) and extracted with ethyl acetate (2×40 ml). The combined organic layers were washed with brine (20 ml), dried (MgSO4) and evaporated. Further purification of the crude product by flash chromatography on silica gel (ethyl acetate/heptane) and crystallization (dichloromethane/hexane) yielded the title compound (65 mg, 36%) as a light yellow solid.

Workup

  1. extractionextracted with ethyl acetate (2×40 ml)
  2. washThe combined organic layers were washed with brine (20 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customFurther purification of the crude product by flash chromatography
  6. customon silica gel (ethyl acetate/heptane) and crystallization (dichloromethane/hexane)

Sources & evidence

ORD record
ord-8fd9b7fb348142c19a718677e71660af
Source dataset
uspto-grants-2013_03
Patent number
US08399674B2

Reaction notes

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