Dimethylacetamide → HCID 62203877, compound

HRID 1971608Notes

Reaction equation

HRID 1971608 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][N:3]=1.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.C[C:21](N(C)C)=[O:22].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[O:10]1[C:11]2[CH:16]=[CH:15][C:14]([C:2]3[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][N:3]=3)=[CH:13][C:12]=2[O:22][CH2:21][CH2:9]1

Participants

7

Reactant 4

HCID 31374DimethylacetamideHCID 62657Potassium Phosphate, TribasicHCID 201262(4-Methoxyphenyl)boronic acidHCID 3457522-Chloro-4-aminopyrimidine

Product 1

HCID 62203877HCID 62203877, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

2-Chloro-pyrimidin-4-ylamine (1 g, 7.7 mmol), 4-methoxybenzeneboronic acid (1.41 g, 9.26 mmol) and dimethylacetamide (12 mL) were added to a microwave tube containing a stirrer bar, potassium phosphate (3.28 g, 15.44 mmol) was dissolved in water (4 mL) and added to the vial. The tetrakis(triphenylphosphine)palladium (0.44 g, 0.386 mmol) was added and the reaction was heated to 150° C. for 10 min. The reaction was filtered through silica and washed through with methanol and concentrated. Yield: 1.10 g, 71%; LCMS method: 1, RT: 3.43 min, MI: 241 [M+1].

Workup

  1. additioncontaining a stirrer bar
  2. additionadded to the vial
  3. filtrationThe reaction was filtered through silica
  4. washwashed through with methanol
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-79538a5aa8d840a388dcec1d7280e2c7
Source dataset
uspto-grants-2013_04
Patent number
US08431596B2

Reaction notes

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