3-Chloropropionyl chloride → 1-(3-Chloro-1-oxopropyl)-1,2-dihydro-4-[3-(trifluoromethyl)phenyl]imidazo[1,5-a]pyrimidine-8-carbonitrile

HRID 1088689Notes

Reaction equation

HRID 1088689 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:4]=[C:5]([C:9]2[N:14]3[CH:15]=[N:16][C:17]([C:18]#[N:19])=[C:13]3[NH:12][CH2:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.CN(C)C1C2C(=CC=CC=2N(C)C)C=CC=1.CN(C)C1C2C(=CC=CC=2N(C)C)C=CC=1.[Cl:54][CH2:55][CH2:56][C:57](Cl)=[O:58]>O1CCCC1>[Cl:54][CH2:55][CH2:56][C:57]([N:12]1[CH2:11][CH:10]=[C:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:20])([F:1])[F:21])[CH:4]=2)[N:14]2[CH:15]=[N:16][C:17]([C:18]#[N:19])=[C:13]12)=[O:58]

Participants

5

Reactant 3

HCID 693643-Chloropropionyl chlorideHCID 14677507HCID 14677507, compoundHCID 22564631HCID 22564631, compound

Product 1

HCID 157125571-(3-Chloro-1-oxopropyl)-1,2-dihydro-4-[3-(trifluoromethyl)phenyl]imidazo[1,5-a]pyrimidine-8-carbonitrileYield 100.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred mixture of 4.5 g of 1,2-dihydro-4-[3-(trifluoromethyl)phenyl]imidazo[1,5-a]pyrimidine-8-carbonitrile (prepared as described in Example 2) and 3.6 g of [1,8-bis(dimethylamino)naphthalene-N,N,N',N'-tetramethyl-1,8-naphthalenediamine] in 120 ml of dry tetrahydrofuran at room temperature, under nitrogen was added over a period of 12-15 minutes a solution of 3.9 g of 3-chloropropionyl chloride in 30 ml of dry tetrahydrofuran. The mixture was stirred at room temperature under nitrogen for one hour then under reflux for 4 hours. The solution was filtered hot and the filtrate was evaporated to dryness in vacuo. The residue was triturated with anhydrous ether and gave 5.95 g of the product of the example as an off-white solid. The product was recrystallized from ethyl acetate, mp 165° 166° C.

Workup

  1. temperatureunder reflux for 4 hours
  2. filtrationThe solution was filtered hot
  3. customthe filtrate was evaporated to dryness in vacuo
  4. customThe residue was triturated with anhydrous ether

Sources & evidence

ORD record
ord-b72b0ecf1e674db9ba29923426d85bba
Source dataset
uspto-grants-1990_10
Patent number
US04963552

Reaction notes

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