Acetone → HCID 57593128, compound

HRID 1785433Notes

Reaction equation

HRID 1785433 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([CH2:9][CH:10]([NH:12][C:13]2[N:18]=[C:17]([N:19]3[C:24]4=[N:25][C:26]([C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)=[CH:27][C:28](=[O:29])[N:23]4[CH2:22][CH2:21][CH2:20]3)[CH:16]=[CH:15][N:14]=2)[CH3:11])[CH:6]=[CH:7][CH:8]=1.[CH3:36][C:37]([CH3:39])=O.[BH4-].[Na+]>>[CH:37]([NH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH2:9][CH:10]([NH:12][C:13]2[N:18]=[C:17]([N:19]3[C:24]4=[N:25][C:26]([C:30]5[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=5)=[CH:27][C:28](=[O:29])[N:23]4[CH2:22][CH2:21][CH2:20]3)[CH:16]=[CH:15][N:14]=2)[CH3:11])[CH:6]=[CH:7][CH:8]=1)([CH3:39])[CH3:36]

Participants

4

Reactant 3

HCID 180AcetoneHCID 4311764Sodium borohydrideHCID 575931519-{2-[2-(3-Aminomethyl-phenyl)-1-methyl-ethylamino]-pyrimidin-4-yl}-2-phenyl-6,7,8,9-tetrahydro-pyrimido[1,2-a]pyrimidin-4-one

Product 1

HCID 57593128HCID 57593128, compound

Procedure

A solution of 9-{2-[2-(3-Aminomethyl-phenyl) -1-methyl-ethylamino]-pyrimidin-4-yl}-2-phenyl-6,7,8,9-tetrahydro -pyrimido[1,2-a]pyrimidin-4-one (79 mg, 0.17 mmol) and acetone (0.015 mL, 0.21 mmol) was stirred for 10 min prior to adding sodium borohydride (108 mg, 3.4 mmol). After 10 min, solvent removed under vacuum and residue partitioned between dichloromethane (10 mL) and saturated sodium chloride. Product isolated as a white solid after purification on silica. M+1=509.

Workup

  1. customsolvent removed under vacuum and residue
  2. custompartitioned between dichloromethane (10 mL) and saturated sodium chloride
  3. customProduct isolated as a white solid
  4. customafter purification on silica

Sources & evidence

ORD record
ord-fc3dbec9aa8e4950a90e014c05e7034c
Source dataset
uspto-grants-2009_03
Patent number
US07504403B2

Reaction notes

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