Sulfuric Acid → HCID 11675422, compound

HRID 900165Notes

Reaction equation

HRID 900165 reaction equation
C([N:4]1[C:8]2[N:9]=[CH:10][N:11]=[C:12]([NH:13][CH2:14][CH:15]3[CH2:19][CH2:18][CH2:17][S:16]3)[C:7]=2[C:6]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:5]1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)C=C.CC(C)([O-])C.[K+].S(=O)(=O)(O)O>CS(C)=O.C(OCC)(=O)C.[Hg](Cl)Cl>[C:20]1([C:6]2[C:7]3[C:12]([NH:13][CH2:14][CH:15]4[CH2:19][CH2:18][CH2:17][S:16]4)=[N:11][CH:10]=[N:9][C:8]=3[NH:4][C:5]=2[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

7

Reactant 3

HCID 1118Sulfuric AcidHCID 23665647Potassium tert-butoxideHCID 69216254HCID 69216254, compound

Product 1

HCID 11675422HCID 11675422, compound

Reagents, catalysts & solvents 3

HCID 24085Mercuric ChlorideCatalystHCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of (7-allyl-5,6-diphenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-(tetrahydrothiophen-2-ylmethyl)-amine (Example 3, Step C, 0.20 mmol) in DMSO (1 mL) was added potassium tert-butoxide (50 mg, 0.45 mmol) and the solution was heated to 110° C. for 24 hours. The solution was then cooled, diluted with ethyl acetate, extracted with water (2×25 mL), dried and concentrated under reduced pressure. Acetone (1 mL) was then added, followed by sulfuric acid (1 N, aq., 1 mL) and mercury (II) chloride (250 mg, 1 mmol). The reaction mixture was heated to reflux for 4 hours, cooled, and purified by preparative HPLC (C8 column, water, acetonitrile, 0.1% TFA) to give the title compound. 1H-NMR (CDCl3): 1.95-1.39 (4 H, m), 2.78-2.57 (2 H, m), 3.75-3.42 (4 H, m), 5.91 (1 H, br s), 7.43-7.02 (10 H, m), 8.20 (1 H, s), 13.87 (1 H, br s). Mass Spectrum (ESI) m/e=387 (M+1).

Workup

  1. temperatureThe solution was then cooled
  2. extractionextracted with water (2×25 mL)
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. additionAcetone (1 mL) was then added
  6. temperatureThe reaction mixture was heated
  7. temperatureto reflux for 4 hours
  8. temperaturecooled
  9. custompurified by preparative HPLC (C8 column, water, acetonitrile, 0.1% TFA)

Sources & evidence

ORD record
ord-f7265f869ebd4b7489b6b8b2aed558d8
Source dataset
uspto-grants-2008_04
Patent number
US07358250B2

Reaction notes

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