Dichloromethane → HCID 118029203, compound

HRID 58149Notes

Reaction equation

HRID 58149 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH2:8][N:9]([CH3:11])[CH3:10])[CH:5]=[CH:4][C:3]=1[NH:12][C:13]1[N:18]=[CH:17][N:16]=[C:15]([N:19]([CH3:43])[C:20]([N:22]([C:31]2[C:36]([Cl:37])=[C:35]([O:38][CH3:39])[CH:34]=[C:33]([O:40][CH3:41])[C:32]=2[Cl:42])COCC[Si](C)(C)C)=[O:21])[CH:14]=1.[C:44](O)([C:46](F)(F)F)=[O:45].[CH2:51](Cl)Cl>>[Cl:42][C:32]1[C:33]([O:40][CH3:41])=[CH:34][C:35]([O:38][CH3:39])=[C:36]([Cl:37])[C:31]=1[NH:22][C:20](=[O:21])[N:19]([C:15]1[N:16]=[CH:17][N:18]=[C:13]([NH:12][C:3]2[CH:4]=[CH:5][C:6]([CH2:8][N:9]([CH3:10])[CH3:11])=[CH:7][C:2]=2[NH:1][C:44](=[O:45])[CH:46]=[CH2:51])[CH:14]=1)[CH3:43]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 1317369731-[6-(2-Amino-4-dimethylaminomethyl-phenylamino)-pyrimidin-4-yl]-3-(2,6-dichloro-3,5-dimethoxy-phenyl)-1-methyl-3-(2-trimethylsilanyl-ethoxymethyl)-urea

Product 1

HCID 118029203HCID 118029203, compoundYield 58%

Procedure

To a stirred solution of 1-[6-(2-amino-4-dimethylaminomethyl-phenylamino)-pyrimidin-4-yl]-3-(2,6-dichloro-3,5-dimethoxy-phenyl)-1-methyl-3-(2-trimethylsilanyl-ethoxymethyl)-urea in anhydrous DCM (10 mL) was added TFA (10 mL) at room temperature. The solution was stirred at room temperature for 3 hours. LCMS showed major product peak. The solution was evaporated to dryness, diluted with DCM (40 mL) and washed with 10% saturated Na2CO3 (10 mL). The DCM layer was dried over anhydrous Na2SO4. Concentration under vacuum gave crude product, which was purified by silica gel column chromatography (10% MeOH/DCM with 0.5% Et3N) to afford the title compound (45 mg, yield: 58% in two steps). MS (ESI): 520 [M+H]+.

Workup

  1. customThe solution was evaporated to dryness
  2. additiondiluted with DCM (40 mL)
  3. washwashed with 10% saturated Na2CO3 (10 mL)
  4. dry with materialThe DCM layer was dried over anhydrous Na2SO4
  5. concentrationConcentration under vacuum
  6. customgave crude product, which
  7. customwas purified by silica gel column chromatography (10% MeOH/DCM with 0.5% Et3N)

Sources & evidence

ORD record
ord-e4c278e7bf27419fbf1e6f2baf6519f7
Source dataset
uspto-grants-2016_09
Patent number
US09434697B2

Reaction notes

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