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Sodium Carbonate → 4-chloro-5-(4-phenoxyphenyl)-7-[1-(1-methyl-4-piperidinyl)-4-piperidinyl]-7H-pyrrolo[2,3-d]pyrimidine

HRID 51617
Notes
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Reaction equation

HRID 51617 reaction equation
N1C2NC=CC=2C=NC=1.[Cl:10][C:11]1[C:12]2[C:19](I)=[CH:18][N:17]([CH:21]3[CH2:26][CH2:25][N:24]([CH:27]4[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]4)[CH2:23][CH2:22]3)[C:13]=2[N:14]=[CH:15][N:16]=1.[O:34]([C:41]1[CH:46]=[CH:45][C:44](B(O)O)=[CH:43][CH:42]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.C(#N)C>[Cl:10][C:11]1[C:12]2[C:19]([C:44]3[CH:45]=[CH:46][C:41]([O:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)=[CH:42][CH:43]=3)=[CH:18][N:17]([CH:21]3[CH2:26][CH2:25][N:24]([CH:27]4[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]4)[CH2:23][CH2:22]3)[C:13]=2[N:14]=[CH:15][N:16]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 2615917H-Pyrrolo(2,3-d)pyrimidineHCID 27343774-Phenoxyphenylboronic acidHCID 227361824-chloro-5-iodo-7-[1-(1-methyl-4-piperidinyl)-4-piperidinyl]-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 227362234-chloro-5-(4-phenoxyphenyl)-7-[1-(1-methyl-4-piperidinyl)-4-piperidinyl]-7H-pyrrolo[2,3-d]pyrimidine
Yield 56.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

1H NMR (DMSO-d6, 400 MHz) 8.62(s, 1H), 8.16(s, 1H), 4.66-4.58(m, 1H), 3.17(s, 1H), 3.02-3.00(d, 2H, J=8 Hz), 2.84-2.82 (d, 2H, J=8 Hz), 2.33-2.26(m, 2H), 2.17 (s, 3H), 2.08-2.04(m, 2H), 1.95-1.85 (m, 4H), 1.91-1.88(d, 2H, J=12 Hz), 1.49-1.45(m, 2H); Waters 2690 Alliance HPLC (Symmetry Shield RP18 3.5 μm, 2.1×50 mm; 5%-95% acetonitrile-0.1 M ammonium acetate over 15 min, 0.5 mL/min) Rt 3.505 min. 4-chloro-5-(4-phenoxyphenyl)-7-1-(1-methyl-4-piperidinyl)-4-piperidinyl]-7H-pyrrolo[2,3-d]pyrimidine A mixture of 4-chloro-5-iodo-7-[ 1-(1-methyl-4-piperidinyl)-4-piperidinyl]-7H-pyrrolo[2,3-d]pyrimidine (0.390 g, 0.845 mmol), 4-phenoxyphenyl boronic acid (0.199 g, 0.93 mmol), tetrakis(triphenylphosphine)pallidium (0.058 g, 0.051 mmol), and sodium carbonate (0.215 g, 2.03 mmol) were heated in a mixture of ethylene glycol dimethyl ether (20 mL) and water (10 mL) at 80° C. for 7 hours under a nitrogen atmosphere. Reaction solution was allowed to cool to room temperature, and the organic layer was removed under reduced pressure. Ethyl acetate was added, the layers were partitioned and the aqueous layer was extracted with ethyl acetate (250 mL). The organic layers were combined, washed with water and brine, dried over magnesium sulfate, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography on silica using 10% methanol in dichloromethane, then 20% methanol in dichloromethane as eluent to give 0.241 g (51%) of 4-chloro-5-(4-phenoxyphenyl)-7-[1-(1-methyl-4-piperidinyl)-4-piperidinyl]-7H-pyrrolo[2,3-d]pyrimidine.

Workup

  1. customReaction solution
  2. customthe organic layer was removed under reduced pressure
  3. additionEthyl acetate was added
  4. customthe layers were partitioned
  5. extractionthe aqueous layer was extracted with ethyl acetate (250 mL)
  6. washwashed with water and brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customThe residue was purified by flash chromatography on silica using 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-06863e454a6f4f95967bfc86066f1f47
Source dataset
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06713474B2

Reaction notes

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