Ethyl Acetate → HCID 86663122, compound

HRID 1019682Notes

Reaction equation

HRID 1019682 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[O:11][CH2:10][CH:9]([NH2:15])[CH2:8]2)=[O:4].Cl[C:17]1[N:22]=[CH:21][C:20]([C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)=[CH:19][N:18]=1.CCOC(C)=O>CN(C=O)C.[Cl-].[Na+].O>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[O:11][CH2:10][CH:9]([NH:15][C:17]1[N:18]=[CH:19][C:20]([C:23]3[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=3)=[CH:21][N:22]=1)[CH2:8]2)=[O:4]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 16244434HCID 16244434, compoundHCID 463153732-Chloro-5-(3-pyridinyl)pyrimidine

Product 1

HCID 86663122HCID 86663122, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of XXXIV (100 mg, 0.48 mmol), 2-chloro-5-pyridin-3-yl-pyrimidine (96 mg, 0.5 mmol) and TEA (137 μl, 1 mmol) in 2 mL of DMF was stirred at 150° C. for 1 h in a microwave reactor. The mixture was worked up with brine and EtOAc, and the organic phase was dried over Na2SO4, filtered, and evaporated in vacuo. Purification by silica gel column gave 80 mg of 3-(5-pyridin-3-yl-pyrimidin-2-ylamino)-chroman-6-carboxylic acid methyl ester XXXXIII (Yield 44%). MS: calc'd 363 (MH+), exp 363 (MH+).

Workup

  1. dry with materialthe organic phase was dried over Na2SO4
  2. filtrationfiltered
  3. customevaporated in vacuo
  4. customPurification by silica gel column

Sources & evidence

ORD record
ord-d74feda4bcd24eff897682f10c877910
Source dataset
uspto-grants-2014_05
Patent number
US08716285B2

Reaction notes

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