Dimethylformamide → HCID 21941884, compound

HRID 2216280Notes

Reaction equation

HRID 2216280 reaction equation
[NH2:1][CH2:2][C:3]1[C:4]([NH:10][CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[N:5][C:6]([Cl:9])=[N:7][CH:8]=1.CCN(C(C)C)C(C)C.CN(C=O)C.[CH3:30][O:31][C:32]1[CH:37]=[CH:36][C:35]([CH2:38][C:39](O)=[O:40])=[CH:34][CH:33]=1>C(OCC)(=O)C>[Cl:9][C:6]1[N:5]=[C:4]([NH:10][CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])[C:3]([CH2:2][NH:1][C:39](=[O:40])[CH2:38][C:35]2[CH:36]=[CH:37][C:32]([O:31][CH3:30])=[CH:33][CH:34]=2)=[CH:8][N:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 76904-Methoxyphenylacetic AcidHCID 81531DiisopropylethylamineHCID 21941873HCID 21941873, compound

Product 1

HCID 21941884HCID 21941884, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.089 g (0.38 mmol) of (5-aminomethyl-2-chloro-pyrimidin-4-yl](2,2-dimethyl-propyl)-amine and 0.27 ml (1.6 mmol) DIEA in 2.5 ml of DMF 0.063 g (0.38 mmol) of (4-methoxy-phenyl)-acetic acid is added and the reaction mixture is stirred at r.t for 16 h. The reaction mixture is then diluted with ethyl acetate and twice washed with H2O, the organic layer is separated and dried over Na2SO4 and then concentrated under reduced pressure. Flash chromatography (ethyl acetate/hexanes 1:1) of the residue provided N-[2-chloro-4-(2,2-dimethyl-propylamino)-pyrimidin-5-ylmethyl]-2-(4-methoxy-phenyl)acetamide as white crystalls.

Workup

  1. washtwice washed with H2O
  2. customthe organic layer is separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-490ae7c557294451893be329c84da399
Source dataset
uspto-grants-2006_09
Patent number
US07112589B2

Reaction notes

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