Acetic Acid → HCID 22636888, compound

HRID 2416306Notes

Reaction equation

HRID 2416306 reaction equation
[F:1][C:2]([F:6])([F:5])[CH2:3][NH2:4].C(O)(=O)C.[NH2:11][C:12]1[N:17]=[C:16]([NH2:18])[C:15]([CH2:19][C:20]2[CH:25]=[C:24]([O:26][CH2:27][CH3:28])[C:23]([C:29]3[CH:34]=[CH:33][C:32]([CH:35]=O)=[CH:31][CH:30]=3)=[C:22]([O:37][CH2:38][CH3:39])[CH:21]=2)=[CH:14][N:13]=1.C([BH3-])#N.[Na+]>CO>[CH2:38]([O:37][C:22]1[CH:21]=[C:20]([CH2:19][C:15]2[C:16]([NH2:18])=[N:17][C:12]([NH2:11])=[N:13][CH:14]=2)[CH:25]=[C:24]([O:26][CH2:27][CH3:28])[C:23]=1[C:29]1[CH:34]=[CH:33][C:32]([CH2:35][NH:4][CH2:3][C:2]([F:6])([F:5])[F:1])=[CH:31][CH:30]=1)[CH3:39]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 9773Ethanamine, 2,2,2-trifluoro-HCID 5003444Sodium cyanoborohydrideHCID 22636879HCID 22636879, compound

Product 1

HCID 22636888HCID 22636888, compoundYield 22.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2,2,2-trifluoroethylamine (0.477 ml; 6 mmol) in 4 ml methanol is adjusted to pH 6 with glacial acetic acid, and 4′-(2,4-diamino-pyrimidin-5-ylmethyl)-2′,6′-diethoxy-biphenyl-4-carbaldehyde (392 mg; 1 mmol) is added. The reaction mixture is then cooled to 0° C. and sodium cyanoborohydride (38 mg; 0.6 mmol) is added. After half and hour at 0° C., the mixture is stirred for 3 h at room temperature. After evaporation of the reaction mixture, the residue is stirred in 20 m water and the mixture is adjusted to pH 8 with 1 N aqueous sodium hydroxide solution. The substance which has precipitated out is filtered off with suction and dried under a high vacuum. The residue is stirred in 20 ml methylene chloride and filtered off with suction again and dried. 105 mg (22%) 5-{2,6-Diethoxy-4′-[(2,2,2-trifluoro-ethylamino)-methyl]-biphenyl-4-ylmethyl}-pyrimidine-2,4-diamine are obtained as a colourless powder.

Workup

  1. additionis added
  2. customAfter evaporation of the reaction mixture
  3. stirringthe residue is stirred in 20 m water
  4. customThe substance which has precipitated out
  5. filtrationis filtered off with suction
  6. customdried under a high vacuum
  7. stirringThe residue is stirred in 20 ml methylene chloride
  8. filtrationfiltered off with suction again
  9. customdried

Sources & evidence

ORD record
ord-2e0fd65260b048cfbe3d1864a198edbf
Source dataset
uspto-grants-2004_11
Patent number
US06821980B1

Reaction notes

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