Morpholine → 8-Chloro-1-(3-{1-[(2-chlorophenyl)methyl]-1H-pyrazol-4-yl}propyl)-3-pentyl-3,7-dihydro-1H-purine-2,6-dione

HRID 1097636Notes

Reaction equation

HRID 1097636 reaction equation
[Cl:1][C:2]1[NH:10][C:9]2[C:8](=[O:11])[N:7]([CH2:12][CH2:13][CH2:14][C:15]3[CH:16]=[N:17][N:18]([CH2:20][C:21]4[CH:26]=[CH:25][C:24](F)=[CH:23][C:22]=4F)[CH:19]=3)[C:6](=[O:29])[N:5]([CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[C:4]=2[N:3]=1.[Cl:35]C1C=CC=CC=1CBr.N1CCOCC1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[NH:10][C:9]2[C:8](=[O:11])[N:7]([CH2:12][CH2:13][CH2:14][C:15]3[CH:16]=[N:17][N:18]([CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[Cl:35])[CH:19]=3)[C:6](=[O:29])[N:5]([CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 11905alpha-Bromo-o-chlorotolueneHCID 593957608-Chloro-1-(3-{1-[(2,4-difluorophenyl)methyl]-1H-pyrazol-4-yl}propyl)-3-pentyl-3,7-dihydro-1H-purine-2,6-dione

Product 1

HCID 593957898-Chloro-1-(3-{1-[(2-chlorophenyl)methyl]-1H-pyrazol-4-yl}propyl)-3-pentyl-3,7-dihydro-1H-purine-2,6-dione

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

Prepared by the method for 8-chloro-1-(3-{1-[(2,4-difluorophenyl)methyl]-1H-pyrazol-4-yl}propyl)-3-pentyl-3,7-dihydro-1H-purine-2,6-dione, Example 6 but from 2-chlorobenzyl bromide (164 mg, 0.8 mmol). However, in order to complete the deprotection step further tetrakis(triphenylphosphine)palladium(0) (40 mg) and morpholine (0.15 ml) were added and stirring continued for a further 5.5 h. Purification by aminopropyl SPE as above afforded the title compound as a solid (42 mg).

Workup

  1. additionwere added
  2. customPurification by aminopropyl SPE as

Sources & evidence

ORD record
ord-d6932e27ef994d5dafac7a1873a3f78c
Source dataset
uspto-grants-2012_03
Patent number
US08143264B2

Reaction notes

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