1,2-Dichloroethane → ethyl 3-(3-((((3aR,4R,6R,6aS)-6-(4-((2,4-dimethoxybenzyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)methyl)(isopropyl)amino)cyclobutyl)propanoate

HRID 511578

Reaction equation

HRID 511578 reaction equation
[CH3:1][O:2][C:3]1[CH:34]=[C:33]([O:35][CH3:36])[CH:32]=[CH:31][C:4]=1[CH2:5][NH:6][C:7]1[C:8]2[CH:15]=[CH:14][N:13]([C@H:16]3[C@H:23]4[C@H:19]([O:20][C:21]([CH3:25])([CH3:24])[O:22]4)[C@@H:18]([CH2:26][NH:27][CH:28]([CH3:30])[CH3:29])[CH2:17]3)[C:9]=2[N:10]=[CH:11][N:12]=1.ClCCCl.O=[C:42]1[CH2:45][CH:44]([CH2:46][CH2:47][C:48]([O:50][CH2:51][CH3:52])=[O:49])[CH2:43]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:34]=[C:33]([O:35][CH3:36])[CH:32]=[CH:31][C:4]=1[CH2:5][NH:6][C:7]1[C:8]2[CH:15]=[CH:14][N:13]([C@H:16]3[C@@H:23]4[O:22][C:21]([CH3:24])([CH3:25])[O:20][C@@H:19]4[C@@H:18]([CH2:26][N:27]([CH:28]([CH3:30])[CH3:29])[CH:42]4[CH2:45][CH:44]([CH2:46][CH2:47][C:48]([O:50][CH2:51][CH3:52])=[O:49])[CH2:43]4)[CH2:17]3)[C:9]=2[N:10]=[CH:11][N:12]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 67775333Ethyl 3-(3-oxocyclobutyl)propanoateHCID 67775374N-(2,4-dimethoxybenzyl)-7-((3aS,4R,6R,6aR)-6-((isopropylamino)methyl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Product 1

HCID 67777277ethyl 3-(3-((((3aR,4R,6R,6aS)-6-(4-((2,4-dimethoxybenzyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)methyl)(isopropyl)amino)cyclobutyl)propanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-(2,4-dimethoxybenzyl)-7-((3aS,4R,6R,6aR)-6-((isopropylamino)methyl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (9.50 g, 15.3 mmol) in 1,2-Dichloroethane (75 mL, 950 mmol) was treated with ethyl 3-(3-oxocyclobutyl)propanoate (3.92 g, 23.0 mmol) and Acetic acid (1.0 mL, 18 mmol) dropwise followed by Sodium triacetoxyborohydride (4.58 g, 21.6 mmol) and the mixture was stirred at RT for 6 days. The reaction mixture was diluted with 150 mL CH2Cl2 and washed with 100 mL sat NaHCO3. The aqueous phase was washed with 100 mL CH2Cl2 and the combined organic phase was dried over Na2SO4, filtered and concentrated to yield a light brown viscous glass.

Workup

  1. washwashed with 100 mL
  2. washThe aqueous phase was washed with 100 mL CH2Cl2
  3. dry with materialthe combined organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto yield a light brown viscous glass

Sources & evidence

ORD record
ord-ac0c563d27084d1496e7a163f47c668d
Source dataset
uspto-grants-2015_08
Patent number
US09096634B2

Linked notes

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