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1-Methylpyrrolidine → 1-(2-Fluoro-4-methyl-5-(7-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-6-yl)phenyl)-3-(4,4,4-trifluoro-3,3-dimethylbutyl)urea

HRID 522722
Notes
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Reaction equation

HRID 522722 reaction equation
CN1CCCC1.[F:7][C:8]1[CH:13]=[C:12]([CH3:14])[C:11]([C:15]2[C:26]([CH3:27])=[N:25][C:18]3[N:19]=[C:20]([S:23][CH3:24])[N:21]=[CH:22][C:17]=3[CH:16]=2)=[CH:10][C:9]=1[NH:28][C:29](=O)[O:30]C(C)=C.Cl.[F:36][C:37]([F:45])([F:44])[C:38]([CH3:43])([CH3:42])[CH2:39][CH2:40][NH2:41]>C1COCC1.CCOC(C)=O>[F:7][C:8]1[CH:13]=[C:12]([CH3:14])[C:11]([C:15]2[C:26]([CH3:27])=[N:25][C:18]3[N:19]=[C:20]([S:23][CH3:24])[N:21]=[CH:22][C:17]=3[CH:16]=2)=[CH:10][C:9]=1[NH:28][C:29]([NH:41][CH2:40][CH2:39][C:38]([CH3:43])([CH3:42])[C:37]([F:45])([F:44])[F:36])=[O:30]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 84541-MethylpyrrolidineHCID 898137724,4,4-Trifluoro-3,3-dimethylbutan-1-amine hydrochlorideHCID 118048013Prop-1-en-2-yl (2-fluoro-4-methyl-5-(7-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-6-yl)phenyl)carbamate

Product 1

HCID 1180360681-(2-Fluoro-4-methyl-5-(7-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-6-yl)phenyl)-3-(4,4,4-trifluoro-3,3-dimethylbutyl)ureaYield 75.1%

Reagents, catalysts & solvents

2
HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

Add 1-methylpyrrolidine (1.214 mL, 11.54 mmol) in a mixture of prop-1-en-2-yl (2-fluoro-4-methyl-5-(7-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-6-yl)phenyl)carbamate (0.92 g, 2.31 mmol) and 4,4,4-trifluoro-3,3-dimethylbutan-1-amine hydrochloride (0.487 g, 2.54 mmol) in THF (23 mL) and heat at 65° C. for 4 h. Cool the mixture to RT, dilute with EtOAc, wash with brine (2×), dry over MgSO4, concentrate to dryness and purify via silica gel chromatography (0-50% EtOAc/Hexanes) to afford the title compound (860 mg, 75% yield). MS (m/z): 496.2 (M+1).

Workup

  1. temperatureCool the mixture to RT
  2. washwash with brine (2×)
  3. dry with materialdry over MgSO4
  4. concentrationconcentrate to dryness
  5. custompurify via silica gel chromatography (0-50% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-e42a8d820ab94b27848eea495bb7a781
Source dataset
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09334267B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes