O-Cresol → HCID 86703929, compound

HRID 1049931Notes

Reaction equation

HRID 1049931 reaction equation
C(OC([N:8]([C:16]1[C:17]2[N:25]=[C:24](Cl)[CH:23]=[CH:22][C:18]=2[N:19]=[CH:20][N:21]=1)C(=O)OC(C)(C)C)=O)(C)(C)C.[CH3:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[OH:34].C(=O)([O-])[O-].[K+].[K+]>CN(C)C1C=CN=CC=1.CC(N(C)C)=O>[C:28]1([CH3:27])[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[O:34][C:24]1[CH:23]=[CH:22][C:18]2[N:19]=[CH:20][N:21]=[C:16]([NH2:8])[C:17]=2[N:25]=1

Participants

6

Reactant 3

HCID 335O-CresolHCID 11430Potassium CarbonateHCID 86703928HCID 86703928, compound

Product 1

HCID 86703929HCID 86703929, compoundYield 53.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

To an 8 mL screw-cap vial was added tert-butyl N-tert-butoxycarbonyl-N-(6-chloropyrido[3,2-d]pyrimidin-4-yl)carbamate 50-A (0.20 mmol, 76 mg) followed by 2-methylphenol (2 equiv., 0.40 mmol, 43 mg), potassium carbonate (2 equiv., 0.40 mmol, 55 mg) and dimethylacetamide (0.4 mL), and 4-dimethylaminopyridine, 0.05 equiv., 0.01 mmol, 1 mg). The reactions were capped and shaken at 80° C. for 2 h. The reaction was filtered, and concentrated via GeneVac. Crude was then taken up in dichloromethane (0.25 mL), followed by trifluoroacetic acid (0.5 mL). The reaction was capped and shaken for 1 h, then concentrated. Crude was purified by reverse phase HPLC to yield 27 mg of product. 1H NMR (400 MHz, DMSO) δ 8.40-8.33 (s, 1H), 8.17-8.11 (d, J=9.0 Hz, 1H), 7.44-7.35 (dd, J=13.1, 8.3 Hz, 2H), 7.32-7.26 (m, 1H), 7.26-7.17 (m, 2H), 2.17-2.13 (s, 3H). LCMS M/Z (M+H)=253.

Workup

  1. customTo an 8 mL screw-cap vial
  2. customThe reactions were capped
  3. filtrationThe reaction was filtered
  4. concentrationconcentrated via GeneVac
  5. customThe reaction was capped
  6. stirringshaken for 1 h
  7. concentrationconcentrated
  8. customCrude was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-bfe3f480e37f4d80b8a89e5617e63025
Source dataset
uspto-grants-2016_07
Patent number
US09382241B2

Reaction notes

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