Acetic Acid → HCID 69047042, compound

HRID 733172Notes

Reaction equation

HRID 733172 reaction equation
O=[CH:2][CH2:3][CH2:4][C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)[N:8]=[C:7]([C:21]#[N:22])[N:6]=1.[NH2:23][CH2:24][CH2:25][CH:26]1[CH2:30][CH2:29][CH2:28][N:27]1[CH3:31].C(O)(=[O:34])C.C([BH3-])#N.[CH3:39][OH:40]>>[F:18][C:17]([F:20])([F:19])[C:39]([OH:34])=[O:40].[CH3:31][N:27]1[CH2:28][CH2:29][CH2:30][CH:26]1[CH2:25][CH2:24][NH:23][CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)[N:8]=[C:7]([C:21]#[N:22])[N:6]=1.[CH3:31][N:27]1[CH2:28][CH2:29][CH2:30][CH:26]1[CH2:25][CH2:24][NH:23][CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)[N:8]=[C:7]([C:21]#[N:22])[N:6]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 887MethanolHCID 983882-(2-Aminoethyl)-1-methylpyrrolidineHCID 498716Cyano-borohydrideHCID 86619632HCID 86619632, compound

Product 2

HCID 69047042HCID 69047042, compoundHCID 86619636HCID 86619636, compound

Procedure

To a stirred solution of 4-(3-oxo-propyl)-6-(3-trifluoromethylphenyl)-pyrimidine-2-carbonitrile (50 mg) in methanol (1 mL) was added 2-(2-Aminoethyl)-1-methylpyrrolidine (48 μL) and acetic acid (12 μL). The mixture was stirred at room temperature for five minutes then solid supported cyanoborohydride (77 mg, 257 mmol/g) was added and stirring continued overnight. The reaction mixture was filtered and the filtrate concentrated under reduced pressure to yield crude product. Purification by preparative-HPLC afforded the TFA salt of 4-{3-[2-(1-methyl-pyrrolidin-2-yl)-ethylamino]-propyl}-6-(3-trifluoromethylphenyl)-pyrimidine-2-carbonitrile.

Workup

  1. additionwas added
  2. stirringstirring continued overnight
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate concentrated under reduced pressure
  5. customto yield crude product
  6. customPurification

Sources & evidence

ORD record
ord-436127aecaa943e0999d135ffe460288
Source dataset
uspto-grants-2009_09
Patent number
US07589095B2

Reaction notes

Loading…