Dimethylamine → HCID 6538982, compound

HRID 987550Notes

Reaction equation

HRID 987550 reaction equation
[O:1]1[CH2:31][CH:2]1[CH2:3][O:4][C:5]1[CH:30]=[CH:29][C:8]([NH:9][C:10]2[CH:15]=[C:14]([N:16]([CH2:25][CH2:26][C:27]#[N:28])[C:17]3[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=3[Cl:24])[N:13]=[CH:12][N:11]=2)=[CH:7][CH:6]=1.[CH3:32][NH:33][CH3:34].O>CN(C=O)C>[CH3:32][N:33]([CH2:31][CH:2]([OH:1])[CH2:3][O:4][C:5]1[CH:30]=[CH:29][C:8]([NH:9][C:10]2[CH:15]=[C:14]([N:16]([CH2:25][CH2:26][C:27]#[N:28])[C:17]3[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=3[Cl:24])[N:13]=[CH:12][N:11]=2)=[CH:7][CH:6]=1)[CH3:34]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 962WaterHCID 18009130HCID 18009130, compound

Product 1

HCID 6538982HCID 6538982, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-{4-[2,3-epoxypropoxy]anilino}-6-[N-(2-cyanoethyl)-2,5-dichloroanilino]pyrimidine (Reference Example 7, 396 mg) in DMF (2 ml) was added dimethylamine (2M in MeOH, 3.5 ml) and the reaction stirred for 6 hours. The mixture was poured into water and extracted with EtOAc. The organic extract was dried (MgSO4) and evaporated. The residue was purified by column chromatography eluting with DCM:MeOH:concentrated ammonia; 91:8:1 to give the product (366 mg, 84%) as a colourless oil. NMR: 2.15 (6H, s), 2.20-2.42 (2H, m), 2.84 (2H, m), 3.72-4.22 (5H, m), 4.77 (1H, d), 5.27 (1H, s), 6.81 (2H, d), 7.37 (2H, d), 7.56 (1H, dd), 7.76 (2H, m), 8.22 (1H, s), 8.88 (1H, s); m/z 501 (MH+).

Workup

  1. extractionextracted with EtOAc
  2. extractionThe organic extract
  3. dry with materialwas dried (MgSO4)
  4. customevaporated
  5. customThe residue was purified by column chromatography
  6. washeluting with DCM

Sources & evidence

ORD record
ord-f17e1db161e94fc7bfcf4bc22d86ac13
Source dataset
uspto-grants-2003_10
Patent number
US06632820B1

Reaction notes

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