Acetic Acid → HCID 86619639, compound

HRID 733201Notes

Reaction equation

HRID 733201 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.[CH:23]1([NH2:26])[CH2:25][CH2:24]1.C(O)(=[O:29])C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH3:45][OH:46]>>[OH:46][C:45]([C:17]([F:20])([F:19])[F:18])=[O:29].[CH:23]1([NH:26][CH2:2][CH2:3][CH2:4][C:5]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=3)[N:8]=[C:7]([C:21]#[N:22])[N:6]=2)[CH2:25][CH2:24]1

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 887MethanolHCID 69828CyclopropylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86619632HCID 86619632, compound

Product 1

HCID 86619639HCID 86619639, compound

Procedure

To a solution of 4-(3-oxo-propyl)-6-(3-trifluoromethylphenyl)-pyrimidine-2-carbonitrile (153 mg) in methanol (2 ml) was added cyclopropylamine (140 μL), acetic acid (0.12 mL), and followed by sodium triacetoxyborohydride (210 mg). The mixture was stirred at room temperature for 24 hours, then purified by preparative-HPLC. 4-(3-cyclopropylamino-propyl)-6-(3-trifluoromethylphenyl)-pyrimidine-2-carbonitrile TFA salt was isolated as a white solid (70 mg).

Workup

  1. custompurified by preparative-HPLC

Sources & evidence

ORD record
ord-93352ec7a621413a96bf353cfeb2d076
Source dataset
uspto-grants-2009_09
Patent number
US07589095B2

Reaction notes

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