Trifluoroacetic acid → 6-[(3R)-3-Aminopiperidin-1-yl]-5-(2-chlorobenzyl)-7-hydroxy-1,3-dimethyl-1H-pyrrolo[3,2-d]pyrimidine-2,4(3H, 5H)dione trifluoroacetate

HRID 1819293Notes

Reaction equation

HRID 1819293 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[Cl:8][C:9]1[CH:43]=[CH:42][CH:41]=[CH:40][C:10]=1[CH2:11][N:12]1[C:20]2[C:19](=[O:21])[N:18]([CH3:22])[C:17](=[O:23])[N:16]([CH3:24])[C:15]=2[C:14]([OH:25])=[C:13]1[N:26]1[CH2:31][CH2:30][CH2:29][C@@H:28]([NH:32]C(=O)OC(C)(C)C)[CH2:27]1>C(Cl)(Cl)Cl>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:32][C@@H:28]1[CH2:29][CH2:30][CH2:31][N:26]([C:13]2[N:12]([CH2:11][C:10]3[CH:40]=[CH:41][CH:42]=[CH:43][C:9]=3[Cl:8])[C:20]3[C:19](=[O:21])[N:18]([CH3:22])[C:17](=[O:23])[N:16]([CH3:24])[C:15]=3[C:14]=2[OH:25])[CH2:27]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57886892tert-butyl {(3R)-1-[5-(2-chlorobenzyl)-7-hydroxy-1,3-dimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidin-6-yl]piperidin-3-yl}carbamate

Product 1

HCID 690736616-[(3R)-3-Aminopiperidin-1-yl]-5-(2-chlorobenzyl)-7-hydroxy-1,3-dimethyl-1H-pyrrolo[3,2-d]pyrimidine-2,4(3H, 5H)dione trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Trifluoroacetic acid (1.5 ml) was added to a solution of tert-butyl {(3R)-1-[5-(2-chlorobenzyl)-7-hydroxy-1,3-dimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidin-6-yl]piperidin-3-yl}carbamate (54 g) in chloroform (1 ml), and the resulting mixture was stirred at room temperature for 2 hours. The reaction solution was concentrated under reduced pressure to obtain the title compound (45 mg).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c1d1e6c0bc224d289b490bcf425fed75
Source dataset
uspto-grants-2009_10
Patent number
US07601728B2

Reaction notes

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