2,2'-Bipyridine → HCID 86696636, compound

HRID 1468620Notes

Reaction equation

HRID 1468620 reaction equation
[CH:1]1(B(O)O)[CH2:3][CH2:2]1.[NH2:7][C:8]1[N:16]=[C:15]2[C:11]([NH:12][C:13](=[O:20])[N:14]2[CH2:17][CH2:18][OH:19])=[C:10]([Cl:21])[N:9]=1.C([O-])([O-])=O.[Na+].[Na+].C1C=CN=C(C2C=CC=CN=2)C=1.[NH4+].[Cl-]>ClC(Cl)C.CN(C)C=O.CC([O-])=O.CC([O-])=O.[Cu+2].O>[NH2:7][C:8]1[N:16]=[C:15]2[C:11]([N:12]([CH:1]3[CH2:3][CH2:2]3)[C:13](=[O:20])[N:14]2[CH2:17][CH2:18][OH:19])=[C:10]([Cl:21])[N:9]=1

Participants

10

Reactant 5

HCID 14742,2'-BipyridineHCID 10340Sodium CarbonateHCID 25517Ammonium ChlorideHCID 2760897Cyclopropylboronic acidHCID 86696631HCID 86696631, compound

Product 1

HCID 86696636HCID 86696636, compoundYield 27%

Reagents, catalysts & solvents 4

HCID 8895Cupric acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 63651,1-DichloroethaneSolvent2×

Conditions

Temperature
70 °C

Procedure

A mixture of cyclopropylboronic acid (0.369 g, 44 mmol), 2-amino-6-chloro-9-(2-hydroxyethyl)-7H-purin-8-one (5 g, 22 mmol) and Na2CO3 (0.462 g, 44 mmol) were taken in dichloroethane (20 ml) and dimethylformamide (10 ml). A suspension of Cu(OAc)2 (0.399 g, 22 mmol) and bipyridine (0.343 g, 22 mmol) in hot dichloroethane (30 ml) was added to the above mixture. The mixture was stirred at 70° C. for 18 hours under air. The resulting mixture was cooled to room temperature, and a saturated aqueous NH4Cl solution was added, followed by water. The organic layer was separated and the aqueous layer was extracted three times with DCM. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated under reduced pressure to get crude 2-amino-6-chloro-7-cyclopropyl-9-(2-hydroxyethyl)purin-8-one (1.6 g, 27%) as an off white solid. 1HNMR (400 MHz, DMSO d6): δ 0.97-1.02 (m, 4H); 2.89-2.92 (m, 1H); 3.61-3.67 (m, 2H); 3.71-3.74 (m, 2H); 4.83 (t, J=12.8 Hz, 1H); 6.67 (bs, 2H)

Workup

  1. additionwas added to the above mixture
  2. temperatureThe resulting mixture was cooled to room temperature
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted three times with DCM
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-10bb719efafc4c3398d8d5c96ddcbcdf
Source dataset
uspto-grants-2015_04
Patent number
US09006177B2

Reaction notes

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