Dimethylamine → tert-Butyl {(3R)-1-[5-(2-chlorobenzyl)-7-[(dimethylamino)methyl]-1,3-dimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidin-6-yl]piperidin-3-yl}carbamate

HRID 1819310Notes

Reaction equation

HRID 1819310 reaction equation
C=O.[CH3:3][NH:4][CH3:5].[Cl:6][C:7]1[CH:40]=[CH:39][CH:38]=[CH:37][C:8]=1[CH2:9][N:10]1[C:18]2[C:17](=[O:19])[N:16]([CH3:20])[C:15](=[O:21])[N:14]([CH3:22])[C:13]=2[CH:12]=[C:11]1[N:23]1[CH2:28][CH2:27][CH2:26][C@@H:25]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:24]1.[C:41]1(C)C=CC=CC=1>C(O)C.C(O)(=O)C>[Cl:6][C:7]1[CH:40]=[CH:39][CH:38]=[CH:37][C:8]=1[CH2:9][N:10]1[C:18]2[C:17](=[O:19])[N:16]([CH3:20])[C:15](=[O:21])[N:14]([CH3:22])[C:13]=2[C:12]([CH2:3][N:4]([CH3:41])[CH3:5])=[C:11]1[N:23]1[CH2:28][CH2:27][CH2:26][C@@H:25]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:34])([CH3:35])[CH3:33])[CH2:24]1

Participants

7

Reactant 4

HCID 674DimethylamineHCID 712FormaldehydeHCID 1140TolueneHCID 57886903tert-Butyl {(3R)-1-[5-(2-chlorobenzyl)-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 57886917tert-Butyl {(3R)-1-[5-(2-chlorobenzyl)-7-[(dimethylamino)methyl]-1,3-dimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidin-6-yl]piperidin-3-yl}carbamate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Paraformaldehyde (600 mg) and a 50% aqueous dimethylamine solution (1.80 g) were added to a solution of tert-butyl {(3R)-1-[5-(2-chlorobenzyl)-1,3-dimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidin-6-yl]piperidin-3-yl}carbamate (1.00 g) in a mixture of ethanol (10 ml) and acetic acid (5 ml), and the resulting mixture was stirred with heating at 80° C. After the reaction solution was cooled to 25° C., toluene (30 ml) was added thereto and the resulting mixture was concentrated under reduced pressure. This procedure was repeated three times. The resulting residue was acidified with a 10% aqueous potassium hydrogensulfate solution and extracted twice with chloroform (100 ml). The organic layer was dried over sodium sulfate and filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by a silica gel column chromatography (hexane/ethyl acetate=1/2) to obtain the title compound (913 mg).

Workup

  1. temperatureAfter the reaction solution was cooled to 25° C.
  2. concentrationthe resulting mixture was concentrated under reduced pressure
  3. extractionextracted twice with chloroform (100 ml)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe resulting residue was purified by a silica gel column chromatography (hexane/ethyl acetate=1/2)

Sources & evidence

ORD record
ord-cf72214f66a84079bdeabca34979ef53
Source dataset
uspto-grants-2009_10
Patent number
US07601728B2

Reaction notes

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