Water → HCID 22249670, compound

HRID 890209Notes

Reaction equation

HRID 890209 reaction equation
C(N(CC)CC)C.[C:8]1([CH3:46])[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[C:9]=1[C:16]1[C:17]([C:37]2C(C)=CC(C)=CC=2C)=[N:18][N:19]2[C:24]3[NH:25][CH2:26][CH2:27][C:23]=3[C:22]([C:28]3C(C)=CC(C)=CC=3C)=[N:21][C:20]=12.[C:47](Cl)(=[O:51])[CH2:48][CH2:49][CH3:50].O>ClCCl>[C:10]1([CH3:15])[CH:11]=[C:12]([CH3:14])[CH:13]=[C:8]([CH3:46])[C:9]=1[C:16]1[C:17]([CH3:37])=[N:18][N:19]2[C:24]3[N:25]([C:47](=[O:51])[CH2:48][CH2:49][CH3:50])[CH2:26][CH2:27][C:23]=3[C:22]([CH3:28])=[N:21][C:20]=12

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 135593034HCID 135593034, compound

Product 1

HCID 22249670HCID 22249670, compoundYield 42.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (0.091 mL, 0.652 mmol) was added to a solution of 3-mesityl-2,5-dimesityl-7,8-dihydro-6H-pyrazolo[1,5-a]pyrrolo[3,2-e]pyrimidine (100 mg, 0.326 mmol) which was prepared in Example 71 in dichloromethane (4 mL), butyryl chloride (0.037 mL, 0.358 mmol) was added dropwise at room temperature, followed by stirring for two hours. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate, washed with brine, and then dried over MgSO4. The solvent was evaporated, and the residue was subjected to silica gel column cromatography (7 g), to give the title compound (52 mg, 42%) as a pale yellow oil from a fraction of ethyl acetate-hexane (1:4 v/v).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-c4d7cac5a74c4a4394202f64cb16dcc7
Source dataset
uspto-grants-2006_02
Patent number
US06995163B2

Reaction notes

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