1,2-Dimethoxyethane → HCID 86666921, compound

HRID 511005Notes

Reaction equation

HRID 511005 reaction equation
Br[C:2]1[C:3]([O:28][CH3:29])=[C:4]([CH:10]([NH:12][C:13]2[N:21]=[CH:20][N:19]=[C:18]3[C:14]=2[N:15]=[CH:16][N:17]3[CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][O:23]2)[CH3:11])[CH:5]=[C:6]([Cl:9])[C:7]=1[F:8].CO[CH2:32][CH2:33]OC.C(=O)([O-])[O-].[K+].[K+].N1C=CC=CC=1.C(B1OB(C=C)OB(C=C)O1)=C>O>[Cl:9][C:6]1[C:7]([F:8])=[C:2]([CH:32]=[CH2:33])[C:3]([O:28][CH3:29])=[C:4]([CH:10]([NH:12][C:13]2[N:21]=[CH:20][N:19]=[C:18]3[C:14]=2[N:15]=[CH:16][N:17]3[CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][O:23]2)[CH3:11])[CH:5]=1

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 27348062,4,6-Trivinylboroxin-Pyridine ComplexHCID 86666918HCID 86666918, compound

Product 1

HCID 86666921HCID 86666921, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of N-[1-(3-bromo-5-chloro-4-fluoro-2-methoxyphenyl)ethyl]-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (50 mg, 0.10 mmol, from Example 187, Step 7) in water (0.21 mL) was added 1,2-dimethoxyethane (0.7 mL), potassium carbonate (14 mg, 0.10 mmol), pyridine:trivinylboroxin (1:1) (26 mg, 0.10 mmol) and tetrakis(triphenylphosphine)Pd(0) (5.2 mg, 0.0045 mmol). The mixture was bubbled with nitrogen for five min and heated at 80° C. overnight. The reaction was diluted with water and EtOAc. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated. Purification on silica gel using 0-100% EtOAc in hexane gave the desired compound (29 mg, 60%). LCMS calculated for C21H24ClFN5O2 (M+H)+: m/z=432.2. found: 432.1.

Workup

  1. customThe mixture was bubbled with nitrogen for five min
  2. additionThe reaction was diluted with water and EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customPurification on silica gel using 0-100% EtOAc in hexane

Sources & evidence

ORD record
ord-06f8e0d52a9d48e9b1bd81fb7adf735b
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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