Water → HCID 14677507, compound

HRID 1088688Notes

Reaction equation

HRID 1088688 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]2[N:14]3[CH:15]=[N:16][C:17]([C:18]#[N:19])=[C:13]3[N:12]=[CH:11][CH:10]=2)[CH:4]=1.C([BH3-])#N.[Na+].O>C(O)(=O)C>[F:20][C:2]([F:1])([F:21])[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

Participants

5

Reactant 3

HCID 962WaterHCID 5003444Sodium cyanoborohydrideHCID 157125564-(alpha,alpha,alpha-Trifluoro-m-tolyl)imidazo[1,5-a]pyrimidine-8-carbonitrile

Product 1

HCID 14677507HCID 14677507, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred mixture of 10.0 g of 4-(α,α,α-trifluoro-m-tolyl)imidazo[1,5-a]pyrimidine-8-carbonitrile (prepared as described in U.S. Pat. No. 4,236,005, Ex. 28) in 150 ml of glacial acetic acid, under nitrogen, at ice bath temperature, was added portionwise 4.15 g of sodium cyanoborohydride. The reaction mixture was stirred in the cold for 30 minutes then at room temperature for 21/2 hours. Then about 50 ml of water was added to the reaction mixture. The precipitate was collected by filtration, washed with water and dried in vacuo to give 8.8 g of the desired product, mp 241°-243° C.

Workup

  1. customprepared
  2. customat room temperature
  3. custom2 hours
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-a6a4c26621a04089b690ff290ff8acf0
Source dataset
uspto-grants-1990_10
Patent number
US04963552

Reaction notes

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