Triethylamine → [4-(4-chlorophenyl)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-piperidin-4-ylmethyl]-methylamine

HRID 2401557Notes

Reaction equation

HRID 2401557 reaction equation
Cl[C:2]1[C:3]2[CH:10]=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.Cl.Cl.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2([CH2:26][NH:27][CH3:28])[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)=[CH:16][CH:15]=1.C(N(CC)CC)C>C(O)CCC>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2([CH2:26][NH:27][CH3:28])[CH2:25][CH2:24][N:23]([C:2]3[C:3]4[CH:10]=[CH:9][NH:8][C:4]=4[N:5]=[CH:6][N:7]=3)[CH2:22][CH2:21]2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-HCID 66873041[4-(4-Chlorophenyl)-piperidin-4-ylmethyl]-methylamine bis-hydrochloride

Product 1

HCID 57899172[4-(4-chlorophenyl)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-piperidin-4-ylmethyl]-methylamineYield 34%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (15.5 mg, 0.1 mmol), [4-(4-chlorophenyl)-piperidin-4-ylmethyl]-methylamine bis-hydrochloride (34 mg, 0.11 mmol) and triethylamine (150 μL, 0.7 mmol) in n-butanol (1 ml) was heated at 100° C. in a microwave reactor for 60 minutes. After cooling the reaction the solvents were concentrated. Purification on SCX-II acid resin, eluting with methanol then 2M ammonia/methanol, followed by further purification by flash column chromatography on silica, eluting with 15% methanol in dichloromethane, gave [4-(4-chlorophenyl)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-piperidin-4-ylmethyl]-methylamine (12.3 mg, 0.034 mmol, 34%). LC-MS (LCT2) m/z 356 [M+H+], Rt 2.64 min.

Workup

  1. temperatureAfter cooling
  2. customthe reaction the solvents
  3. concentrationwere concentrated
  4. customPurification on SCX-II acid resin
  5. washeluting with methanol
  6. custom2M ammonia/methanol, followed by further purification by flash column chromatography on silica
  7. washeluting with 15% methanol in dichloromethane

Sources & evidence

ORD record
ord-fb613228c2dd44d597cdb14b499ade94
Source dataset
uspto-grants-2014_08
Patent number
US08796293B2

Reaction notes

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