Dimethylbarbituric acid → HCID 68488633, compound

HRID 1630511Notes

Reaction equation

HRID 1630511 reaction equation
C([N:4]1[CH2:25][CH2:24][C:7]2[N:8]([CH:16]=[CH:17][C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)[C:9]3[CH:10]=[CH:11][C:12]([CH3:15])=[CH:13][C:14]=3[C:6]=2[CH2:5]1)C=C.CN1C(=O)CC(=O)N(C)C1=O>C(Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:15][C:12]1[CH:11]=[CH:10][C:9]2[N:8]([CH:16]=[CH:17][C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)[C:7]3[CH2:24][CH2:25][NH:4][CH2:5][C:6]=3[C:14]=2[CH:13]=1

Participants

5

Reactant 2

HCID 69860Dimethylbarbituric acidHCID 68283240HCID 68283240, compound

Product 1

HCID 68488633HCID 68488633, compoundYield 4.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

2-Allyl-8-methyl-5-(2-(pyridin-4-yl)vinyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (50 mg, 0.151 mmol) was dissolved in DCM (2 mL), which was degassed with nitrogen for 15 min. To this was added Pd(PPh3)4 (4 mg, 0.002 mmol) followed by 1,3-dimethyl barbituric acid (71 mg, 0.454 mmol). The reaction mixture was again degassed by nitrogen for 15 min. The resultant mixture was stirred at RT for 1 h. DCM was evaporated in vacuo. EtOAc (20 mL) was added to reaction mixture and was washed with saturated potassium carbonate solution (3×1 mL). The organic layer was dried over anhydrous sodium sulfate, evaporated in vacuo and purified by reverse phase HPLC to obtain 2 mg of 8-methyl-5-(2-(pyridin-4-yl)vinyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole. 1H NMR (CD3OD, Free base): δ (ppm): 8.45 (d, 2H), 8.0 (d, 1H), 7.7 (d, 1H), 7.58 (d, 2H), 7.3 (s, 1H), 7.19 (d, 1H), 6.8 (d, 1H), 4.29 (s, 2H), 3.42 (m, 2H), 3.2 (m, 2H), 2.4 (s, 3H).

Workup

  1. customwhich was degassed with nitrogen for 15 min
  2. customThe reaction mixture was again degassed by nitrogen for 15 min
  3. customDCM was evaporated in vacuo
  4. additionEtOAc (20 mL) was added to reaction mixture
  5. washwas washed with saturated potassium carbonate solution (3×1 mL)
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. customevaporated in vacuo
  8. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-a4637cb84c69405097c2585e26b52543
Source dataset
uspto-grants-2014_07
Patent number
US08791132B2

Reaction notes

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