HCID 10156642, compound → HCID 9969179, compound

HRID 1831622Notes

Reaction equation

HRID 1831622 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][N:5]([C:8]1[C:9]2[CH:17]([CH3:18])[C:16](=O)[N:15]([C:20]3[C:25]([CH3:26])=[CH:24][C:23]([CH3:27])=[CH:22][C:21]=3[CH3:28])[C:10]=2[N:11]=[C:12]([CH3:14])[N:13]=1)[CH2:6][CH3:7].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:4]([N:5]([C:8]1[C:9]2[CH:17]([CH3:18])[CH2:16][N:15]([C:20]3[C:25]([CH3:26])=[CH:24][C:23]([CH3:27])=[CH:22][C:21]=3[CH3:28])[C:10]=2[N:11]=[C:12]([CH3:14])[N:13]=1)[CH2:6][CH3:7])[CH2:3][CH2:2][CH3:1]

Participants

4

Reactant 2

HCID 10156642HCID 10156642, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 9969179HCID 9969179, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (4-butyl-ethyl-amino)-2,5-dimethyl-7-(2,4,6-trimethylphenyl)-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one) (111 mg, 0.292 mmol) in dry THF was treated with lithium aluminum hydride at room temperature. The resulting mixture was heated at reflux for 5 hours. After standard work-up, 97 mg of crude material as an oil was obtained. The oil was purified through a chromatotron using 10% ethyl acetate in hexane as eluent to give butyl-[2,5-dimethyl-7-(2,4,6-trimethylphenyl)-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl]-ethylamine as a clear pale yellow oil. 1H NMR (CDCl3) δ 6.91 (d, 2H), 3.7–3.9 (m, 2H), 3.2–3.4 (m, 4H), 2.5 (q, 1H), 2.28 (s, 6H), 2.22 (s, 3H), 2.05 (s, 3H), 1.5–1.7 (m, 2H), 1.3–1.5 (m, 5H), 1.17 (t, 3H), 0.97 (t, 3H) ppm. High MS (C23H34N4) calc. 366.2776, found 366.27622.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 5 hours
  3. customAfter standard work-up, 97 mg of crude material as an oil was obtained
  4. customThe oil was purified through a chromatotron

Sources & evidence

ORD record
ord-a240177bd6af452aa76fe7305563f696
Source dataset
uspto-grants-2006_06
Patent number
US07067664B1

Reaction notes

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