1,2-Dimethoxyethane → HCID 86697427, compound

HRID 1478258Notes

Reaction equation

HRID 1478258 reaction equation
Br[C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[CH:9][C:8]([NH:11][CH2:12][CH2:13][N:14]([CH3:21])[C:15](=[O:20])[O:16][CH:17]([CH3:19])[CH3:18])=[N:7][C:6]=12.O.O.[CH3:24][O:25][C:26]1[CH:27]=[N:28][CH:29]=[CH:30][C:31]=1B(O)O.[O-]P([O-])([O-])=O.[K+].[K+].[K+].COCCOC>CCOC(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[CH3:24][O:25][C:26]1[CH:27]=[N:28][CH:29]=[CH:30][C:31]=1[C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[CH:9][C:8]([NH:11][CH2:12][CH2:13][N:14]([CH3:21])[C:15](=[O:20])[O:16][CH:17]([CH3:19])[CH3:18])=[N:7][C:6]=12

Participants

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 62657Potassium Phosphate, TribasicHCID 86697428HCID 86697428, compoundHCID 86697429HCID 86697429, compound

Product 1

HCID 86697427HCID 86697427, compoundYield 77%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 80 mg (0.22 mmol) of isopropyl (2-((3-bromopyrazolo[1,5-a]pyrimidin-5-yl)amino)ethyl)(methyl)-carbamate was added (3-methoxypyridin-4-yl)boronic acid dihydrate (56 mg, 0.27 mmol), K3PO4 (143 mg, 0.67 mmol), PdCl2(PPh3)2 (16.8 mg, 0.022 mmol), 3 mL of DME and 1 mL of water. This mixture was microwaved at 140° C. for 0.5 hr. After cooling, it was diluted with EtOAc, and washed with water and brine. The organic layer was dried over MgSO4, concentrated, and purified on the PREP HPLC to afford the desired product in 77% yield (66.4 mg). 1H NMR (400 MHz, Acetone) δ ppm 2.87 (br. s., 3 H) 2.99 (br. s., 3 H) 3.58-3.71 (m, 2 H) 3.73-3.82 (m, 2 H) 4.09 (s, 3 H) 4.82 (td, J=6.25, 2.91 Hz, 1 H) 6.45 (br. s., 1 H) 8.21 (br. s., 1 H) 8.35 (s, 1 H) 8.43 (d, J=6.06 Hz, 1 H) 8.58 (s, 1 H) 8.77 (br. s., 1 H); LRMS (ESI) m/e 385.0 [(M+H)+, calcd for C19H24N6O3 384.0].

Workup

  1. customThis mixture was microwaved at 140° C. for 0.5 hr
  2. temperatureAfter cooling
  3. washwashed with water and brine
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. custompurified on the PREP HPLC

Sources & evidence

ORD record
ord-4228de854fd241b6b2ce873f43812576
Source dataset
uspto-grants-2016_08
Patent number
US09403832B2

Reaction notes

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