Triethylamine → HCID 86726549, compound

HRID 870605Notes

Reaction equation

HRID 870605 reaction equation
[C:1](Cl)(=[O:7])[O:2][CH2:3][CH2:4][CH2:5][Cl:6].[CH2:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH:10]1[NH:18][C:19]1[N:20]=[CH:21][C:22]2[CH2:28][NH:27][CH2:26][CH2:25][C:23]=2[N:24]=1.C(N(CC)CC)C>O1CCCC1.ClCCl.C(=O)(O)[O-].[Na+]>[CH2:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH:10]1[NH:18][C:19]1[N:20]=[CH:21][C:22]2[CH2:28][N:27]([C:1]([O:2][CH2:3][CH2:4][CH2:5][Cl:6])=[O:7])[CH2:26][CH2:25][C:23]=2[N:24]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 69399Carbonochloridic acid, 3-chloropropyl esterHCID 86726522N-(indan-2-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine

Product 1

HCID 86726549HCID 86726549, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

Add a solution of 3-chloropropyl carbonochloridate (0.55 mL; 1.2 equiv; 4.51 mmoles) in tetrahydrofuran (25 mL) over 1 hour to a mixture of N-indan-2-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine (1.00 g; 1.0 equiv; 3.75 mmoles) and triethylamine (1.10 mL; 2.1 equiv; 7.88 mmoles) in tetrahydrofuran (25 mL). Stir for 2 hours, then dilute with dichloromethane and saturated sodium bicarbonate and separate the layers. Further extract the aqueous layer with dichloromethane (2×). Dry the combined organic extracts over sodium sulfate, filter, and concentrated to dryness to give a yellow oil. Purify the crude product by column chromatography (10% methanol in dichloromethane) to 3-chloropropyl 2-(indan-2-ylamino)-7,8-dihydro-5H-pyrido[4,3-d]pyrimidine-6-carboxylate (1.146 g; 79%): MS (m/z): 387(M+1).

Workup

  1. customseparate the layers
  2. extractionFurther extract the aqueous layer with dichloromethane (2×)
  3. dry with materialDry the combined organic extracts over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrated to dryness
  6. customto give a yellow oil
  7. customPurify the crude product by column chromatography (10% methanol in dichloromethane) to 3-chloropropyl 2-(indan-2-ylamino)-7,8-dihydro-5H-pyrido[4,3-d]pyrimidine-6-carboxylate (1.146 g; 79%)

Sources & evidence

ORD record
ord-a40e6953ee4c433eb45e1cbb1436a6ec
Source dataset
uspto-grants-2015_03
Patent number
US08969555B2

Reaction notes

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