Diisopropylethylamine → HCID 178524241, compound

HRID 396270Notes

Reaction equation

HRID 396270 reaction equation
[CH:1]1([CH2:7][N:8]2[C:15]([NH2:16])=[C:14]([NH2:17])[C:12](=[O:13])[N:11]([CH2:18][CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[C:9]2=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C[O:26][C:27]([C:29]1[CH:30]=[CH:31][C:32]([C:35](O)=O)=[N:33][CH:34]=1)=[O:28].C(N(C(C)C)CC)(C)C>ClCCl>[CH:19]1([CH2:18][N:11]2[C:12](=[O:13])[C:14]3[N:17]=[C:35]([C:32]4[CH:31]=[CH:30][C:29]([C:27]([OH:28])=[O:26])=[CH:34][N:33]=4)[NH:16][C:15]=3[N:8]([CH2:7][CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)[C:9]2=[O:10])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 3149925-(Methoxycarbonyl)pyridine-2-carboxylic acidHCID 222449751,3-Bis(cyclohexylmethyl)-5,6-diaminouracil

Product 1

HCID 178524241HCID 178524241, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 1,3-bis(cyclohexylmethyl)-5,6-diaminouracil (1.45 g, 4.33 mmol), from Example 1, part (d) above, in dichloromethane (25 mL) was added the intermediate 5-(methoxycarbonyl)pyridine-2-carboxylic acid (1.78 g, 5.52 mmol) and diisopropylethylamine (Aldrich, 0.84 g, 6.5 mmol). This reaction mixture was stirred at room temperature for 4 hours. The reaction mixture was concentrated under reduced pressure and the crude material was taken up in 1N sodium hydroxide and heated to reflux for 3 hours. The reaction mixture was cooled to room temperature, diluted with acetic acid and the product precipitated from the reaction mixture to provide 6-(1,3-Bis(cyclohexylmethyl)-1,2,3,6-tetrahydro-2,6-dioxo-9H-purin-8-yl)nicotinic Acid (1.44 g, 56%) as a green solid. 1H-NMR (300 MHz, DMSO-d6) δ: 9.68 (s, 1H), 9.10 (d, J=3.1 Hz, 1H), 8.43 (m, 1H), 8.12 (m, 1H), 6.71 (br s, 1H), 4.12-3.60 (br m, 4H), 1.80-1.40 (m, 11H), 1.35-0.91 (m, 11H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. temperatureheated
  3. temperatureto reflux for 3 hours
  4. temperatureThe reaction mixture was cooled to room temperature
  5. additiondiluted with acetic acid
  6. customthe product precipitated from the reaction mixture

Sources & evidence

ORD record
ord-33a072aec38e4f359489a9d6b2d41b8c
Source dataset
uspto-grants-2003_08
Patent number
US06608069B1

Reaction notes

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