(R)-ethyl 5-(2-(2-(3-(tert-butoxycarbonylamino)prop-1-ynyl)-5-fluoropyridin-3-yl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate → (R)-ethyl 5-(2-(2-(3-aminopropyl)-5-fluoropyridin-3-yl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate

HRID 1426968Notes

Reaction equation

HRID 1426968 reaction equation
C(OC([NH:8][CH2:9][C:10]#[C:11][C:12]1[C:17]([C@H:18]2[CH2:22][CH2:21][CH2:20][N:19]2[C:23]2[CH:28]=[CH:27][N:26]3[N:29]=[CH:30][C:31]([C:32]([O:34][CH2:35][CH3:36])=[O:33])=[C:25]3[N:24]=2)=[CH:16][C:15]([F:37])=[CH:14][N:13]=1)=O)(C)(C)C>CO.O[Pd]O>[NH2:8][CH2:9][CH2:10][CH2:11][C:12]1[C:17]([C@H:18]2[CH2:22][CH2:21][CH2:20][N:19]2[C:23]2[CH:28]=[CH:27][N:26]3[N:29]=[CH:30][C:31]([C:32]([O:34][CH2:35][CH3:36])=[O:33])=[C:25]3[N:24]=2)=[CH:16][C:15]([F:37])=[CH:14][N:13]=1

Participants

4

Reactant 1

HCID 86691750(R)-ethyl 5-(2-(2-(3-(tert-butoxycarbonylamino)prop-1-ynyl)-5-fluoropyridin-3-yl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate

Product 1

HCID 86691751(R)-ethyl 5-(2-(2-(3-aminopropyl)-5-fluoropyridin-3-yl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylateYield 108%

Reagents, catalysts & solvents 2

HCID 178526213HCID 178526213, compoundCatalystHCID 887MethanolSolvent

Procedure

To (R)-ethyl 5-(2-(2-(3-(tert-butoxycarbonylamino)prop-1-ynyl)-5-fluoropyridin-3-yl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate (160 mg, 0.315 mmol) in MeOH (10 mL) was added dihydroxypalladium (101 mg, 0.144 mmol). The reaction mixture was stirred under a hydrogen balloon for 6 hours, then filtered through a pad of Celite® and washed with MeOH (30 mL). The filtrate was concentrated and the resultant residue was treated with 4 M HCl in dioxane (3 mL). After stirring for 30 minutes, the solution was concentrated to afford the product as an HCl salt (140 mg, 108% yield). MS (apci) m/z=413.0 (M+H).

Workup

  1. filtrationfiltered through a pad of Celite®
  2. washwashed with MeOH (30 mL)
  3. concentrationThe filtrate was concentrated
  4. additionthe resultant residue was treated with 4 M HCl in dioxane (3 mL)
  5. stirringAfter stirring for 30 minutes
  6. concentrationthe solution was concentrated

Sources & evidence

ORD record
ord-dc52fb8dc37a4297938a90b4f9ea8616
Source dataset
uspto-grants-2015_01
Patent number
US08933084B2

Reaction notes

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