Water → HCID 57530525, compound

HRID 2243735Notes

Reaction equation

HRID 2243735 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][N:11]([CH3:13])[CH3:12])[N:5]=[C:4]2[N:14]([C:19]3[C:24]([F:25])=[CH:23][CH:22]=[CH:21][C:20]=3[F:26])[C:15](=[O:18])[NH:16][CH2:17][C:3]=12.O.C(=O)([O-])[O-].[K+].[K+].[CH3:34][C:35]([O:38][C:39]([C:41]1[CH:42]=[C:43]([F:51])[C:44]([CH3:50])=[C:45](B(O)O)[CH:46]=1)=[O:40])([CH3:37])[CH3:36]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:26][C:20]1[CH:21]=[CH:22][CH:23]=[C:24]([F:25])[C:19]=1[N:14]1[C:4]2[N:5]=[C:6]([NH:8][CH2:9][CH2:10][N:11]([CH3:13])[CH3:12])[N:7]=[C:2]([C:45]3[CH:46]=[C:41]([CH:42]=[C:43]([F:51])[C:44]=3[CH3:50])[C:39]([O:38][C:35]([CH3:34])([CH3:36])[CH3:37])=[O:40])[C:3]=2[CH2:17][NH:16][C:15]1=[O:18]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 11951693HCID 11951693, compoundHCID 59671639HCID 59671639, compound

Product 1

HCID 57530525HCID 57530525, compoundYield 93.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 5-chloro-1-(2,6-difluorophenyl)-7-{[2-(dimethylamino)ethyl]amino}-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one (200 mg, 0.52 mmol) in dioxane (15 mL)/water (5 mL) were added potassium carbonate (433 mg, 3.14 mmol), tetrakis(triphenylphosphine)palladium(0) (31 mg, 0.027 mmol) and (5-{[(1,1-dimethylethyl)oxy]carbonyl}-3-fluoro-2-methylphenyl)boronic acid (159 mg, 0.63 mmol). The reaction mixture was bubbled with N2 for 10 mins, then microwaved at 150° C. for 30 mins. The reaction mixture was concentrated. To the concentrated mixture were added DMSO (2 mL), H2O (0.5 mL) and AcOH (0.05 mL). Separation via a HPLC then provided the title compound as a white solid (270 mg, 88%). LC-MS m/z 587 (M+H)+.

Workup

  1. customThe reaction mixture was bubbled with N2 for 10 mins
  2. custommicrowaved at 150° C. for 30 mins
  3. concentrationThe reaction mixture was concentrated
  4. additionTo the concentrated mixture were added DMSO (2 mL), H2O (0.5 mL) and AcOH (0.05 mL)
  5. customSeparation via a HPLC

Sources & evidence

ORD record
ord-123fa186562c4eabaab249e3611420c3
Source dataset
uspto-grants-2010_03
Patent number
US07674789B2

Reaction notes

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