Sodium borohydride → HCID 22636813, compound

HRID 2416316Notes

Reaction equation

HRID 2416316 reaction equation
[BH4-].[Na+].[NH2:3][C:4]1[N:9]=[C:8]([NH2:10])[C:7]([CH2:11][C:12]2[CH:17]=[C:16]([O:18][CH2:19][CH3:20])[C:15]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)=[C:14]([O:29][CH2:30][C:31]3(/[CH:34]=[CH:35]/[C:36]#[N:37])[CH2:33][CH2:32]3)[CH:13]=2)=[CH:6][N:5]=1>C(O)(C)C>[NH2:3][C:4]1[N:9]=[C:8]([NH2:10])[C:7]([CH2:11][C:12]2[CH:17]=[C:16]([O:18][CH2:19][CH3:20])[C:15]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)=[C:14]([O:29][CH2:30][C:31]3([CH2:34][CH2:35][C:36]#[N:37])[CH2:33][CH2:32]3)[CH:13]=2)=[CH:6][N:5]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 22636828HCID 22636828, compound

Product 1

HCID 22636813HCID 22636813, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Sodium borohydride (45 mg; 1.2 mmol) is added to (E)-3-[1-[4-(2,4-diamino-pyrimidin-5-ylmethyl)-6-ethoxy-4′-methoxy-biphenyl-2-yloxymethyl]-cyclopropyl]-acrylonitrile (220 mg; 0.467 mmol) in isopropanol (25 ml) and the mixture is stirred for 19 hours under reflux. The reaction mixture is concentrated, the residue is stirred with water (15 ml), the mixture is adjusted to pH 2 with 1 N aqueous hydrochloric acid and back to pH 9 with conc. NH4OH and filtered with suction and the residue is dried under a high vacuum. The crude product is chromatographed over silica gel (20 g) with methylene chloride/methanol/NH4OH conc. (19/1/0.05). The pure fractions are concentrated together and the residue is stirred with diethyl ether, filtered off with suction and dried under a high vacuum. 75 mg (34%) 3-{1-[4-(2,4-diamino-pyrimidin-5-ylmethyl)-6-ethoxy-4′-methoxy-biphenyl-2-yloxymethyl]-cyclopropyl}-propionitrile are obtained as a colourless powder.

Workup

  1. temperatureunder reflux
  2. concentrationThe reaction mixture is concentrated
  3. stirringthe residue is stirred with water (15 ml)
  4. filtrationfiltered with suction
  5. customthe residue is dried under a high vacuum
  6. customThe crude product is chromatographed over silica gel (20 g) with methylene chloride/methanol/NH4OH conc. (19/1/0.05)
  7. concentrationThe pure fractions are concentrated together
  8. stirringthe residue is stirred with diethyl ether
  9. filtrationfiltered off with suction
  10. customdried under a high vacuum

Sources & evidence

ORD record
ord-fbf140bb1f3f40abb9ce2b59ac500eec
Source dataset
uspto-grants-2004_11
Patent number
US06821980B1

Reaction notes

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