Aniline → HCID 18009134, compound

HRID 987553Notes

Reaction equation

HRID 987553 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]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[F:24])[N:13]=[CH:12][N:11]=2)=[CH:7][CH:6]=1.NC1C=CC=CC=1.CC(C)([O-])C.[Na+].Br[CH2:42][CH2:43][F:44]>CN(C=O)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]([CH2:42][CH2:43][F:44])[C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[F:24])[N:13]=[CH:12][N:11]=2)=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 6115AnilineHCID 129822-Fluoroethyl bromideHCID 18009143HCID 18009143, compoundHCID 23676156Sodium t-butoxide

Product 1

HCID 18009134HCID 18009134, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-[4-(2,3-epoxypropoxy)anilino]-6-(2,4-difluoroanilino)pyrimidine (prepared by an analogous procedure to Reference Examples 9 and using the appropriate aniline) (1.4 g) in DMF (11 ml) at 0° C. was added sodium tert-butoxide (580 mg) and the mixture stirred for 10 minutes. To a portion of this solution (2.2 ml) was added 1-bromo-2-fluoroethane (0.11 ml) and the reaction stirred for 1 hour. The solution was then 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; 125:2 to give the product (237 mg, 75%) as a colourless oil. NMR: 2.65 (2H, m), 2.81 (2H, m), 3.79 (1H, dd), 4.01-4.18 (2H, m), 4.51 (2H, t), 4.67 (2H, t), 5.40 (1H, s), 6.82 (2H, d), 7.21 (1H, m), 7.30-7.59 (4H, m), 8.20 (1H, s), 8.84 (1H, s).

Workup

  1. customat 0° C.
  2. stirringthe reaction stirred for 1 hour
  3. extractionextracted with EtOAc
  4. extractionThe organic extract
  5. dry with materialwas dried (MgSO4)
  6. customevaporated
  7. customThe residue was purified by column chromatography
  8. washeluting with DCM

Sources & evidence

ORD record
ord-4c4c5e7343a042109f6003cf45c8dd32
Source dataset
uspto-grants-2003_10
Patent number
US06632820B1

Reaction notes

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