Sodium Carbonate → HCID 67382064, compound

HRID 910205Notes

Reaction equation

HRID 910205 reaction equation
Br[C:2]1[C:10]2[C:9]([NH:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)=[N:8][C:7]([N:19]([CH2:23][CH2:24][OH:25])[CH2:20][CH2:21][OH:22])=[N:6][C:5]=2[S:4][C:3]=1[CH3:26].[C:27]1(B(O)O)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(COC)OC>[OH:22][CH2:21][CH2:20][N:19]([C:7]1[N:8]=[C:9]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[C:10]2[C:2]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[C:3]([CH3:26])[S:4][C:5]=2[N:6]=1)[CH2:23][CH2:24][OH:25]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 66827Phenylboronic AcidHCID 67381992HCID 67381992, compound

Product 1

HCID 67382064HCID 67382064, compoundYield 22%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Procedure

In a 10 ml glass tube were placed 2-[{5-bromo-6-methyl-4-[(pyridin-2-ylmethyl)amino]thieno[2,3-d]pyrimidin-2-yl}-(2-hydroxyethyl)amino]ethanol (32 mg, 0.073 mmol), phenylboronic acid (20 mg, 0.166 mmol), sodium carbonate (26 mg, 0.249 mmol), triphenylphosphine (7 mg, 0.025 mmol), palladium(II)acetate (2 mg, 0.008 mmol), dimethoxyethane (0.75 ml) and water (0.25 ml). The tube was sealed with a septum and placed in the microwave cavity. Microwave irradiation of 200 W was used, the temperature being ramped from room temperature to 150° C. Once 150° C. was reached, the reaction mixture was held at this temperature for 1 hour. The resultant mixture was diluted with water (50 ml), extracted into dichloromethane (3×50 ml) and the combined organic extracts were dried (MgSO4). The solvent was removed in vacuo to give the crude product which was purified by flash chromatography (silica) eluting with ethyl acetate followed by 5% methanol in ethyl acetate to give 2-((2-hydroxyethyl)-{6-methyl-5-phenyl-4-[(pyridin-2-ylmethyl)amino]thieno[2,3-d]pyrimidin-2-yl}amino)ethanol as a brown gum (7 mg).

Workup

  1. customIn a 10 ml glass tube were placed
  2. customThe tube was sealed with a septum
  3. customMicrowave irradiation of 200 W
  4. custombeing ramped from room temperature to 150° C
  5. customOnce 150° C.
  6. extractionextracted into dichloromethane (3×50 ml)
  7. dry with materialthe combined organic extracts were dried (MgSO4)
  8. customThe solvent was removed in vacuo
  9. customto give the crude product which
  10. customwas purified by flash chromatography (silica)
  11. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-037f3380953b498d9424857b37b823ac
Source dataset
uspto-grants-2011_09
Patent number
US08022076B2

Reaction notes

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