Dimethylamine → HCID 18009144, compound

HRID 987551Notes

Reaction equation

HRID 987551 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.CC(C)([O-])C.[K+].[CH3:34][O:35][C:36]1[CH:43]=[CH:42][C:39]([CH2:40]Br)=[CH:38][CH:37]=1.[CH3:44][NH:45][CH3:46]>CN(C=O)C.O>[CH3:44][N:45]([CH2:27][CH:2]([OH: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]([CH2:40][C:39]3[CH:42]=[CH:43][C:36]([O:35][CH3:34])=[CH:37][CH:38]=3)[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)[CH3:46]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 1650214-Methoxybenzyl bromideHCID 18009127HCID 18009127, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 18009144HCID 18009144, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-{4-[2,3-epoxypropoxy]anilino}-6-(2,5-dichloroanilino)pyrimidine (Reference Example 9; 316 ma) in DMF (3 ml) was added potassium tert-butoxide (1M solution in tetrahydrofuran. 0.86 ml) at −35° C. and the solution stirred for 30 minutes. 4-Methoxybenzyl bromide (0.32 ml) was then added and the solution allowed to warm to ambient temperature over 2.5 hours. After stirring for 1 hour at ambient temperature, dimethylamine (2M in MeOH, 2 ml) was added and the reaction stirred for a further 18 hours. 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:concentrated ammonia; 91:8:1 to give the title compound (220 mg, 49%) as a colourless oil. NMR: 2.19 (6H, s), 2.21-2.40 (2H, m), 3.68-3.92 (6H, m), 4.76 (1H, m), 4.95 (2H, brs), 5.38 (1H, s), 6.81 (4H, m), 7.19 (2H, m), 7.35 (3H, m), 7.42 (1H, dd), 7.61 (1H; d), 8.21 (1H, s), 8.83 (1H, s); m/z 568 (MH+).

Workup

  1. stirringAfter stirring for 1 hour at ambient temperature
  2. stirringthe reaction stirred for a further 18 hours
  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-410227234046438fa6897f1f69597754
Source dataset
uspto-grants-2003_10
Patent number
US06632820B1

Reaction notes

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