Pyrrolidine → HCID 11254863, compound

HRID 898130Notes

Reaction equation

HRID 898130 reaction equation
[CH2:1]([S:7][C:8]1[N:13]=[C:12]([CH:14]=O)[CH:11]=[C:10]([CH3:16])[N:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[NH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1.C([BH3-])#N.[Na+]>C(O)C.C(O)(=O)C>[CH2:1]([S:7][C:8]1[N:9]=[C:10]([CH3:16])[CH:11]=[C:12]([CH2:14][N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[N:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 3

HCID 31268PyrrolidineHCID 5003444Sodium cyanoborohydrideHCID 16050184HCID 16050184, compound

Product 1

HCID 11254863HCID 11254863, compoundYield 28.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

2-Hexylsulfanyl-6-methyl-pyrimidine-4-carbaldehyde (0.1 g, 0.42 mmol) was dissolved in ethanol (1 mL) and acetic acid (0.1 mL). Then pyrrolidine (0.07 mL, 1 mmol) and sodium cyanoborohydride (26 mg, 0.4 mmol) were added slowly at 20° C. and stirring continued for 24 h. The reaction mixture was evaporated to dryness and dissolved in a minimal amount of DMF (0.8 mL) and directly purified by preparative HPLC chromatography on a YMC combiprep ODS-AQ column (75×20 mm iD, S-5 μM, 12 nm) with an acetonitrile-water gradient. One obtained 34.7 mg (28%) of a yellow liquid. MS: m/z=294 (M+H).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. dissolutiondissolved in a minimal amount of DMF (0.8 mL)
  3. customdirectly purified by preparative HPLC chromatography on a YMC combiprep ODS-AQ column (75×20 mm iD

Sources & evidence

ORD record
ord-f98ea223a89e4659a210bc5579ca9d5d
Source dataset
uspto-grants-2008_04
Patent number
US07351700B2

Reaction notes

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