Triethylamine → 3-Chloropropyl 2-(indan-2-ylamino)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylate

HRID 870599Notes

Reaction equation

HRID 870599 reaction equation
[C:1](Cl)(=[O:7])[O:2][CH2:3][CH2:4][CH2:5][Cl:6].O.Cl.Cl.[CH2:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH:13]1[NH:21][C:22]1[N:23]=[CH:24][C:25]2[CH2:30][NH:29][CH2:28][C:26]=2[N:27]=1.C(N(CC)CC)C>O1CCCC1.ClCCl>[CH2:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:12][CH:13]1[NH:21][C:22]1[N:23]=[CH:24][C:25]2[CH2:30][N:29]([C:1]([O:2][CH2:3][CH2:4][CH2:5][Cl:6])=[O:7])[CH2:28][C:26]=2[N:27]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 69399Carbonochloridic acid, 3-chloropropyl esterHCID 86726534N-(2,3-dihydro-1H-inden-2-yl)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-amine dihydrochloride hydrate

Product 1

HCID 867265623-Chloropropyl 2-(indan-2-ylamino)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylateYield 100.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Add a solution of 3-chloropropyl carbonochloridate (0.55 mL; 1.48 equiv; 4.54 mmoles) in tetrahydrofuran (21 mL) dropwise over 1 hour to a mixture of N-(2,3-dihydro-1H-inden-2-yl)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-amine dihydrochloride hydrate (1.0 g; 1.0 equiv; 3.07 mmoles) and triethylamine (2.2 mL; 5.1 equiv; 15.78 mmoles) in tetrahydrofuran (21 mL). Stir the solution for 18 hours, then dilute with dichloromethane and wash with sodium bicarbonate solution. Further extract the aqueous layer with dichloromethane (2×). Dry the combined organic extracts over sodium sulfate, filter, and concentrate to afford 3-chloropropyl 2-(indan-2-ylamino)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylate (1.15 g; 100%) as a brown solid: MS (m/z): 373(M+1).

Workup

  1. washwash with sodium bicarbonate solution
  2. extractionFurther extract the aqueous layer with dichloromethane (2×)
  3. dry with materialDry the combined organic extracts over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-8abc660695a14709aa402b66588318c5
Source dataset
uspto-grants-2015_03
Patent number
US08969555B2

Reaction notes

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