3-Bromo-1-propanol → 2-adamantan-1-yl-N-[7-(3-hydroxy-propyl)-5,6,7,8-tetrahydro-pyrido[3,4-d]pyrimidin-4-yl]-acetamide

HRID 1593592Notes

Reaction equation

HRID 1593592 reaction equation
[C:1]12([CH2:11][C:12]([NH:14][C:15]3[C:16]4[CH2:24][CH2:23][NH:22][CH2:21][C:17]=4[N:18]=[CH:19][N:20]=3)=[O:13])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.Br[CH2:26][CH2:27][CH2:28][OH:29].CCN(C(C)C)C(C)C>CCO>[C:1]12([CH2:11][C:12]([NH:14][C:15]3[C:16]4[CH2:24][CH2:23][N:22]([CH2:26][CH2:27][CH2:28][OH:29])[CH2:21][C:17]=4[N:18]=[CH:19][N:20]=3)=[O:13])[CH2:2][CH:3]3[CH2:4][CH:5]([CH2:6][CH:7]([CH2:9]3)[CH2:8]1)[CH2:10]2

Participants

5

Reactant 3

HCID 123083-Bromo-1-propanolHCID 81531DiisopropylethylamineHCID 248565612-adamantan-1-yl-N-(5,6,7,8-tetrahydro-pyrido[3,4-d]pyrimidin-4-yl)-acetamide

Product 1

HCID 118477002-adamantan-1-yl-N-[7-(3-hydroxy-propyl)-5,6,7,8-tetrahydro-pyrido[3,4-d]pyrimidin-4-yl]-acetamideYield 17%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-adamantan-1-yl-N-(5,6,7,8-tetrahydro-pyrido[3,4-d]pyrimidin-4-yl)-acetamide (0.05 g, 0.153 mmol), 3-bromo-1-propanol (0.021 g, 0.15 mmol) and DIPEA (0.045 g, 0.35 mmol) in EtOH (4 mL) was stirred at 75° C. for 17 h. The reaction vessel was allowed to cool to room temperature, opened, and the volatiles were removed on a rotary evaporator. The residue was redissolved in THF (3 mL). PL-NCO resin (300 mg) was added, and the resulting suspension was stirred at room temperature for 16 h. The resin was filtered and the volatiles were removed under vacuum. The crude product was purified by HPLC to afford 2-adamantan-1-yl-N-[7-(3-hydroxy-propyl)-5,6,7,8-tetrahydro-pyrido[3,4-d]pyrimidin-4-yl]-acetamide (0.0098 g, 17%).

Workup

  1. customthe volatiles were removed on a rotary evaporator
  2. dissolutionThe residue was redissolved in THF (3 mL)
  3. additionPL-NCO resin (300 mg) was added
  4. filtrationThe resin was filtered
  5. customthe volatiles were removed under vacuum
  6. customThe crude product was purified by HPLC

Sources & evidence

ORD record
ord-cb4355c3770d4b20a59fd3a300d29a32
Source dataset
uspto-grants-2007_11
Patent number
US07297700B2

Reaction notes

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