Water → HCID 18009130, compound

HRID 987552Notes

Reaction equation

HRID 987552 reaction equation
[O:1]1[CH2:27][CH:2]1[CH2:3][O:4][C:5]1[CH:26]=[CH:25][C:8]([NH:9][C:10]2[CH:15]=[C:14]([NH:16][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.C([O-])([O-])=O.[K+].[K+].Br[CH2:35][CH2:36][C:37]#[N:38].O>CS(C)=O>[O:1]1[CH2:27][CH:2]1[CH2:3][O:4][C:5]1[CH:26]=[CH:25][C:8]([NH:9][C:10]2[CH:15]=[C:14]([N:16]([CH2:35][CH2:36][C:37]#[N:38])[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

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 170203-BromopropionitrileHCID 18009127HCID 18009127, compound

Product 1

HCID 18009130HCID 18009130, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 4-{4-[2,3-epoxypropoxy]anilino}-6-(2,5-dichloroanilino)pyrimidine (Reference Example 9, 1.4 g) in DMSO (3.75 ml) was added K2CO3 (1.1 g) and 3-bromopropionitrile (0.66 ml) and the reaction stirred for 20 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; 99:1 to give the product (436 mg, 26%) as a colourless oil. NMR: 2.66 (1H, t), 2.78-2.92 (3H, m), 3.76 (1H, dd), 3.82-4.36 (3H, m), 5.28 (1H, s), 6.82 (2H, d), 7.38 (2H, d), 7.57 (1H, dd), 7.72 (1H, m), 8.25 (1H, s), 8.89 (1H, s); m/z 456(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-38938cf56b9b4f63bc00756ad34f142c
Source dataset
uspto-grants-2003_10
Patent number
US06632820B1

Reaction notes

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