Ammonia → HCID 71731206, compound

HRID 522739Notes

Reaction equation

HRID 522739 reaction equation
[CH3:1][C:2]([CH3:31])([CH3:30])[CH2:3][CH2:4][NH:5][C:6]([NH:8][C:9]1[CH:14]=[C:13]([C:15]2[C:26]([CH3:27])=[N:25][C:18]3[N:19]=[C:20](SC)[N:21]=[CH:22][C:17]=3[CH:16]=2)[C:12]([CH3:28])=[CH:11][C:10]=1[F:29])=[O:7].C1C=C(Cl)C=C(C(OO)=O)C=1.[NH3:43]>C(Cl)Cl>[NH2:43][C:20]1[N:21]=[CH:22][C:17]2[CH:16]=[C:15]([C:13]3[C:12]([CH3:28])=[CH:11][C:10]([F:29])=[C:9]([NH:8][C:6]([NH:5][CH2:4][CH2:3][C:2]([CH3:31])([CH3:30])[CH3:1])=[O:7])[CH:14]=3)[C:26]([CH3:27])=[N:25][C:18]=2[N:19]=1

Participants

5

Reactant 3

HCID 222Ammonia2×HCID 70297m-Chloroperbenzoic acidHCID 898134311-(3,3-Dimethylbutyl)-3-(2-fluoro-4-methyl-5-(7-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-6-yl)phenyl)urea

Product 1

HCID 71731206HCID 71731206, compoundYield 24.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Treat a suspension of 1-(3,3-dimethylbutyl)-3-(2-fluoro-4-methyl-5-(7-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-6-yl)phenyl)urea (0.248 g, 0.562 mmol) in DCM (20 mL) with 70 wt % mCPBA (0.208 g, 0.842 mmol) and stir the mixture at RT for 2 h. Add ammonia (0.5N in dioxane, 8.99 mL, 4.49 mmol) and stir the mixture at RT overnight. Add additional ammonia (7N in MeOH, 5 mL, 35 mmol) and stir at RT overnight. Concentrate the mixture to dryness, treat with saturated. Na2CO3 and extract with DCM (4×). Dry the combined organics over MgSO4, concentrate to dryness and purify via silica gel chromatography (50-100% EtOAc/Hex, then 0-10% MeOH/EtOAc) to afford the title compound as an off-white solid (57 mg, 24%). MS (m/z): 411.2 (M+1).

Workup

  1. additionTreat
  2. stirringstir at RT overnight
  3. concentrationConcentrate the mixture to dryness
  4. additiontreat with saturated
  5. extractionNa2CO3 and extract with DCM (4×)
  6. dry with materialDry the combined organics over MgSO4
  7. concentrationconcentrate to dryness
  8. custompurify via silica gel chromatography (50-100% EtOAc/Hex

Sources & evidence

ORD record
ord-58f759d8829b419991ad7adeeb3d7e06
Source dataset
uspto-grants-2016_05
Patent number
US09334267B2

Reaction notes

Loading…