Triphenylphosphine → Tert-butyl (S)-3-(4-chloro-5-iodo-7H-pyrrolo[2,3-D]pyrimidin-7-YL)pyrrolidine-1-carboxylate

HRID 516159Notes

Reaction equation

HRID 516159 reaction equation
CC(OC(/N=N/C(OC(C)C)=O)=O)C.[Cl:15][C:16]1[C:17]2[C:24]([I:25])=[CH:23][NH:22][C:18]=2[N:19]=[CH:20][N:21]=1.[C:26]([N:33]1[CH2:37][CH2:36][C@@H:35](O)[CH2:34]1)([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[Cl:15][C:16]1[C:17]2[C:24]([I:25])=[CH:23][N:22]([C@H:36]3[CH2:35][CH2:34][N:33]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:37]3)[C:18]=2[N:19]=[CH:20][N:21]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 6544479tert-Butyl (3R)-3-hydroxypyrrolidine-1-carboxylateHCID 148092816-Chloro-7-iodo-7-deazapurine

Product 1

HCID 44141157Tert-butyl (S)-3-(4-chloro-5-iodo-7H-pyrrolo[2,3-D]pyrimidin-7-YL)pyrrolidine-1-carboxylateYield 64.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

DIAD (1.41 ml) was added to a solution of 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (1.00 g), (R)—N-Boc-3-pyrrolidinol (1.01 g), and triphenylphosphine (1.88 g) in tetrahydrofuran (40 ml), and the reaction mixture was stirred for 1 hour. The reaction mixture was concentrated and washed with ethyl acetate to obtain the title compound as a white solid (1.04 g). Physical properties: m/z [M+H]+ 448.9

Workup

  1. concentrationThe reaction mixture was concentrated
  2. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-fa9bbd0c05b942b592eb562f8feb0e53
Source dataset
uspto-grants-2015_08
Patent number
US09108973B2

Reaction notes

Loading…