Dimethylamine → HCID 21912089, compound

HRID 1831624Notes

Reaction equation

HRID 1831624 reaction equation
[CH2:1]([N:5]([CH2:26][CH3:27])[C:6]1[C:7]2[CH2:15][C:14](=[O:16])[N:13]([C:17]3[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][C:18]=3[CH3:25])[C:8]=2[N:9]=[C:10]([CH3:12])[N:11]=1)[CH2:2][CH2:3][CH3:4].[O:28]=P(Cl)(Cl)Cl.C(N(CC)CC)C.CNC>C(#N)C>[CH2:1]([N:5]([CH2:26][CH3:27])[C:6]1[C:7]2[C:15](=[O:28])[C:14](=[O:16])[N:13]([C:17]3[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][C:18]=3[CH3:25])[C:8]=2[N:9]=[C:10]([CH3:12])[N:11]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 21912073HCID 21912073, compound

Product 1

HCID 21912089HCID 21912089, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-(butyl-ethyl-amino)-2-methyl-7-(2,4,6-trimethyphenyl)-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one (76 mg, 0.207 mmol), POCl3 (0.039 ml, 0.415 mmol), triethylamine (0.059 ml), and dimethylamine (1 ml) in 2 ml acetonitrile was heated at reflux for 1 hour. The mixture was quenched with water and extracted with ethyl acetate. The organic layer was dried and concentrated to give a brown form (105 mg). After silica gel column chromatography, the title compound was isolated as a yellow glass (10 mg). 1H NMR (CDCl3) δ 7.00 (s, 2H), 3.95–4.15 (m, 2H), 3.65–3.85 (m, 2H), 2.38 (s, 3H), 2.32 (s, 3H), 2.10 (s, 6H), 1.55–1.75 (m, 2H), 1.35–1.55 (m, 2H), 1.25 (t, 3H), 1.00 (t, 3H) ppm.

Workup

  1. temperatureat reflux for 1 hour
  2. customThe mixture was quenched with water
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was dried
  5. concentrationconcentrated
  6. customto give a brown form (105 mg)

Sources & evidence

ORD record
ord-90647194048e46d8b847ef053dd979a1
Source dataset
uspto-grants-2006_06
Patent number
US07067664B1

Reaction notes

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