Dimethylbarbituric acid → HCID 68284170, compound

HRID 2408607Notes

Reaction equation

HRID 2408607 reaction equation
C([N:4]1[CH2:16][CH2:15][C:14]2[N:13]([CH2:17][CH:18]([C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)[OH:19])[C:12]3[N:11]=[CH:10][C:9]([CH3:26])=[CH:8][C:7]=3[C:6]=2[CH2:5]1)C=C.CN1C(=O)CC(=O)N(C)C1=O>C(Cl)Cl.C(=O)([O-])[O-].[K+].[K+].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>[CH3:26][C:9]1[CH:10]=[N:11][C:12]2[N:13]([CH2:17][CH:18]([C:20]3[CH:21]=[CH:22][N:23]=[CH:24][CH:25]=3)[OH:19])[C:14]3[CH2:15][CH2:16][NH:4][CH2:5][C:6]=3[C:7]=2[CH:8]=1

Participants

6

Reactant 2

HCID 69860Dimethylbarbituric acidHCID 68283772HCID 68283772, compound

Product 1

HCID 68284170HCID 68284170, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolventHCID 11430Potassium CarbonateSolvent

Procedure

To a degassed solution of 2-(6-allyl-3-methyl-5,6,7,8-tetrahydro-1,6,9-triaza-fluoren-9-yl)-1-pyridin-4-yl-ethanol (300 mg, 0.862 mmol) and 1,3 dimethyl barbituric acid (403 mg, 2.586 mmol) in DCM (7 mL) was added and Pd(PPh3)4 (20 mg, 0.0172 mmol) and the reaction mixture stirred at RT for 1 h. The progress of reaction was monitored by TLC and LCMS. The reaction mixture was diluted with 20% aq potassium carbonate solution and extracted with DCM (3×25 mL). The combined organic layer was washed with 20% aq potassium carbonate solution, dried over anhydrous sodium sulfate and concentrated to yield 2-(3-methyl-5,6,7,8-tetrahydro-1,6,9-triaza-fluoren-9-yl)-1-pyridin-4-yl-ethanol. 1H NMR (CDCl3, freebase) δ (ppm): 8.5 (d, 2H), 8.03 (s, 1H), 7.51 (s, 1H), 7.22 (d, 2H) 5.14 (d, 1H), 4.4 (dd, 1H), 4.27 (dd, 1H), 3.93 (q, 2H), 3.13 (m, 2H), 2.54 (dd, 1H), 2.42 (s, 3H), 2.3 (dd, 1H). Separation by chiral HPLC provided enantiomers 58a and 58b.

Workup

  1. customThe progress of reaction
  2. extractionextracted with DCM (3×25 mL)
  3. washThe combined organic layer was washed with 20% aq potassium carbonate solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-10269cf165ef4ed9b49f5433a777df7d
Source dataset
uspto-grants-2014_08
Patent number
US08815843B2

Reaction notes

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