1,2-Dimethoxyethane → HCID 59334007, compound

HRID 1927008Notes

Reaction equation

HRID 1927008 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[C:10]3[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:14]([CH3:25])([CH3:24])[C:11]=3[NH:12][N:13]=2)[C:5]([F:26])=[CH:4][N:3]=1.[CH3:27][C:28]1(C)C(C)(C)OB(C=C)O1.C([O-])([O-])=O.[Na+].[Na+].COCCOC>C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe].O>[F:26][C:5]1[C:6]([NH:8][C:9]2[C:10]3[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:14]([CH3:25])([CH3:24])[C:11]=3[NH:12][N:13]=2)=[N:7][C:2]([CH:27]=[CH2:28])=[N:3][CH:4]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 52330122-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 57519194HCID 57519194, compound

Product 1

HCID 59334007HCID 59334007, compound

Reagents, catalysts & solvents 2

HCID 53485975CID 53485975CatalystHCID 962WaterSolvent

Procedure

To a septum capped sealed tube was added tert-butyl 3-[(2-chloro-5-fluoropyrimidin-4-yl)amino]-6,6-dimethyl-4,6-dihydropyrrolo[3,4-c]pyrazole-5(1H)-carboxylate (2.00 g, 5.22 mmol), 4,4,5,5-tetramethyl-2-vinyl-1,3,2 dioxaborolane (2.41 g, 15.7 mmol), Na2CO3 (1.66 g, 15.7 mmol) and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (850 mg, 1.04 mmol) followed by DME (50 mL) and water (12 mL). The reaction mixture was purged with argon for 2 min. then placed in a preheated 100° C. oil bath and stirred for 16 h. The crude reaction was concentrated then taken up in EtOAc (100 mL) and washed with water (50 mL). The EtOAc solution was dried (MgSO4), filtered and concentrated. Purification was performed by silica gel column chromatography using 1-10% 7N NH3/MeOH in CH2Cl2 to provided the desired compound E1(i) as an orange solid (1.8 g, 91%). 1H NMR (300 MHz, CDCl3) δ ppm 1.45-1.58 (m, 9H), 1.65-1.78 (m, 6H), 4.45-4.71 (m, 2H), 5.58-5.71 (m, 1H), 6.34-6.46 (m, 1H), 6.68-6.82 (m, 1H), 7.99 (s, 1H), 8.12-8.32 (m, 1H). Mass spectrum: Calcd for C18H24FN6O2 (M+H): 375. Found 375.

Workup

  1. customTo a septum capped
  2. customsealed tube
  3. customThe reaction mixture was purged with argon for 2 min.
  4. customthen placed in a preheated 100° C.
  5. customThe crude reaction
  6. concentrationwas concentrated
  7. washwashed with water (50 mL)
  8. dry with materialThe EtOAc solution was dried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customPurification

Sources & evidence

ORD record
ord-d29e944236bf410680e444af7e1f39f5
Source dataset
uspto-grants-2012_05
Patent number
US08183255B2

Reaction notes

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