Triethylamine → 1-[2-(indan-2-ylamino)-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl]prop-2-en-1-one

HRID 870579Notes

Reaction equation

HRID 870579 reaction equation
C(N(CC)CC)C.[C:8](Cl)(=[O:11])[CH:9]=[CH2:10].[CH2:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH:14]1[NH:22][C:23]1[N:24]=[CH:25][C:26]2[CH2:32][NH:31][CH2:30][CH2:29][C:27]=2[N:28]=1>ClCCl>[CH2:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH:14]1[NH:22][C:23]1[N:24]=[CH:25][C:26]2[CH2:32][N:31]([C:8](=[O:11])[CH:9]=[CH2:10])[CH2:30][CH2:29][C:27]=2[N:28]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 86726522N-(indan-2-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine

Product 1

HCID 867265401-[2-(indan-2-ylamino)-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl]prop-2-en-1-oneYield 70.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Add triethylamine (0.82 mL; 2.0 equiv; 5.86 mmoles) followed by 2-propenoyl chloride (0.24 mL; 1.0 equiv; 2.93 mmoles) dropwise to a 0° C. solution of N-indan-2-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine (0.781 g; 1.0 equiv; 2.93 mmoles) in dichloromethane (29 mL). Stir the solution for 16 hours at ambient temperature, then dilute with dichloromethane, wash with brine, dry over sodium sulfate, filter, and concentrate to an orange oil. Purify the crude product by column chromatography to afford 1-[2-(indan-2-ylamino)-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl]prop-2-en-1-one (0.66 g; 70%): MS (m/z): 321 (M+1).

Workup

  1. washwash with brine
  2. dry with materialdry over sodium sulfate
  3. filtrationfilter
  4. concentrationconcentrate to an orange oil
  5. customPurify the crude product by column chromatography

Sources & evidence

ORD record
ord-964ca580b8484b91aab2b9410d0a8af3
Source dataset
uspto-grants-2015_03
Patent number
US08969555B2

Reaction notes

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