Diisopropylethylamine → HCID 58999592, compound

HRID 1593588Notes

Reaction equation

HRID 1593588 reaction equation
[CH2:1]([N:8]1[CH2:17][CH2:16][C:15]2[C:14]([NH2:18])=[N:13][CH:12]=[N:11][C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[C:28]12([C:38](Cl)=[O:39])[CH2:37][CH:32]3[CH2:33][CH:34]([CH2:36][CH:30]([CH2:31]3)[CH2:29]1)[CH2:35]2>C(Cl)(Cl)Cl>[CH2:1]([N:8]1[CH2:17][CH2:16][C:15]2[C:14]([NH:18][C:38]([C:28]34[CH2:37][CH:32]5[CH2:31][CH:30]([CH2:36][CH:34]([CH2:33]5)[CH2:35]3)[CH2:29]4)=[O:39])=[N:13][CH:12]=[N:11][C:10]=2[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 989151-Adamantanecarbonyl chlorideHCID 58999587HCID 58999587, compound

Product 1

HCID 58999592HCID 58999592, compoundYield 41.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
160 °C

Procedure

In a 20 ml microwave vessel was added 7-benzyl-5,6,7,8-tetrahydro-pyrido[3,4-d]pyrimidin-4-ylamine (1.5 g, 6.3 mmole) in 7.0 ml of chloroform, diisopropylethylarnine (2.2 ml, 12.6 mmole) and 1-adamantane carbonylchloride (2.51 g, 12.6 mmole). The reaction was heated at 160° C. for 7.0 minutes in a microwave. After completion the solvent was evaporated and the residue was dissolved in EtOAc and washed with sat. NaHCO3, washed with brine and dried over sodium sulphate. The solvents were removed under reduced pressure and the residue was chromatographed using chloroform (100%) to give the desired product as a white solid (1.06 g).

Workup

  1. customAfter completion the solvent was evaporated
  2. dissolutionthe residue was dissolved in EtOAc
  3. washwashed with sat. NaHCO3
  4. washwashed with brine
  5. dry with materialdried over sodium sulphate
  6. customThe solvents were removed under reduced pressure
  7. customthe residue was chromatographed

Sources & evidence

ORD record
ord-40df5cb051a343448fc93783491a9814
Source dataset
uspto-grants-2007_11
Patent number
US07297700B2

Reaction notes

Loading…