Triethylamine → HCID 178441811, compound

HRID 705126Notes

Reaction equation

HRID 705126 reaction equation
[CH2:1]([C:5]1[N:6]=[C:7]([NH:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][C:24]=2[O:31][CH3:32])[C:8]2[NH:13][N:12]=[C:11]([C:14]#[C:15][CH2:16][CH2:17][CH2:18][CH2:19]Cl)[C:9]=2[N:10]=1)[CH2:2][CH2:3][CH3:4].[NH:33]1[CH2:37][CH2:36][CH2:35][CH2:34]1.CCN(CC)CC>C(#N)C>[CH2:1]([C:5]1[N:6]=[C:7]([NH:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][C:24]=2[O:31][CH3:32])[C:8]2[NH:13][N:12]=[C:11]([C:14]#[C:15][CH2:16][CH2:17][CH2:18][CH2:19][N:33]3[CH2:37][CH2:36][CH2:35][CH2:34]3)[C:9]=2[N:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31268Pyrrolidine2×HCID 178441809HCID 178441809, compound

Product 1

HCID 178441811HCID 178441811, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 5-butyl-3-(6-chlorohex-1-yn-1-yl)-N-(2,4-dimethoxybenzyl)-1H-pyrazolo[4,3-d]pyrimidin-7-amine (30 g, 65.8 mmol), pyrrolidine (16.32 mL, 197 mmol) and Et3N (27.5 mL, 197 mmol) in Acetonitrile (400 mL) was heated at 70° C. for 16 hours. Further pyrrolidine (7 g) was added and the solution was heated at 70° C. for 8 hours. The cooled solution was evaporated and the residue was purified on a silica cartridge (750 g) eluted with EtOAc (2 column volumes) followed by 20-30% MeOH (+1% Et3N)/EtOAc (16 column volumes) to give the title compound as a yellow gum (23.3 g).

Workup

  1. customThe cooled solution was evaporated
  2. customthe residue was purified on a silica cartridge (750 g)
  3. washeluted with EtOAc (2 column volumes)

Sources & evidence

ORD record
ord-4b69849e7dfb49f5828aa9a58e260472
Source dataset
uspto-grants-2015_11
Patent number
US09173872B2

Reaction notes

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