Potassium Carbonate → HCID 59605435, compound

HRID 1946139Notes

Reaction equation

HRID 1946139 reaction equation
Br.Br[CH2:3][C:4]1[N:5]([CH3:30])[C:6]2[C:11]([N:12]=1)=[C:10]([N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)[N:9]=[C:8]([N:19]1[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[N:21]=[C:20]1[CH2:28][CH3:29])[N:7]=2.[CH3:31][S:32]([N:35]1[CH2:40][C@@H:39]([CH3:41])[NH:38][C@@H:37]([CH3:42])[CH2:36]1)(=[O:34])=[O:33].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:42][C@@H:37]1[CH2:36][N:35]([S:32]([CH3:31])(=[O:34])=[O:33])[CH2:40][C@H:39]([CH3:41])[N:38]1[CH2:3][C:4]1[N:5]([CH3:30])[C:6]2[C:11]([N:12]=1)=[C:10]([N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)[N:9]=[C:8]([N:19]1[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[N:21]=[C:20]1[CH2:28][CH3:29])[N:7]=2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 66617827HCID 66617827, compoundHCID 67492640HCID 67492640, compound

Product 1

HCID 59605435HCID 59605435, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 8-bromomethyl-2-(2-ethylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purine hydrobromide (200 mg, 0.37 mmol), (3S,5R)-1-methanesulfonyl-3,5-dimethylpiperazine (88 mg, 0.46 mmol) and K2CO3 (150 mg, 1.09 mmol) in DMF (1 mL) was allowed to stir at r.t. for 24 h. The reaction mixture was partitioned between EtOAc and H2O, the organic phase dried (MgSO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, MeOH:EtOAc, 0-10%) followed by recrystallisation from EtOAc affording 737 (57 mg, 28%). LCMS (method I): RT 3.05 min, [M+H]+ 568.2. 1H NMR (CDCl3, 400 MHz): δ 8.02-7.98 (1 H, m), 7.76-7.75 (1 H, m), 7.26-7.25 (2 H, m), 4.34 (4 H, s), 4.18 (2 H, s), 3.87 (4 H, t, J=4.70 Hz), 3.84 (3 H, s), 3.54-3.51 (2 H, m), 3.35 (2 H, q, J=7.48 Hz), 3.29-3.23 (2 H, m), 2.80 (3 H, s), 2.68-2.66 (2 H, m), 1.45 (3 H, dd, J=7.69, 7.26 Hz), 1.17 (6 H, d, J=6.36 Hz)

Workup

  1. customThe reaction mixture was partitioned between EtOAc and H2O
  2. dry with materialthe organic phase dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe resulting residue was purified by column chromatography (Si—PCC, MeOH:EtOAc, 0-10%)
  5. customfollowed by recrystallisation from EtOAc affording 737 (57 mg, 28%)
  6. customRT 3.05 min, [M+H]+ 568.2

Sources & evidence

ORD record
ord-350b6b36f074466e8e3a13855c1ffc2e
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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