Ammonia → HCID 59299542, compound

HRID 2386632Notes

Reaction equation

HRID 2386632 reaction equation
[CH2:1]([N:5]1[C:13](=[O:14])[C:12]2[N:11]([CH2:15][CH:16]=[CH2:17])[C:10]([C:18](O)=[O:19])=[N:9][C:8]=2[N:7]([CH2:21][CH2:22][CH2:23][CH3:24])[C:6]1=[O:25])[CH2:2][CH2:3][CH3:4].CC[N:28](C(C)C)C(C)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.N>CN(C=O)C>[CH2:1]([N:5]1[C:13](=[O:14])[C:12]2[N:11]([CH2:15][CH:16]=[CH2:17])[C:10]([C:18]([NH2:28])=[O:19])=[N:9][C:8]=2[N:7]([CH2:21][CH2:22][CH2:23][CH3:24])[C:6]1=[O:25])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 59299595HCID 59299595, compound

Product 1

HCID 59299542HCID 59299542, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 1,3-dibutyl-2,6-dioxo-7-(2-propen-1-yl)-2,3,6,7-tetrahydro-1H-purine-8-carboxylic acid (1.0 g, 2.9 mmol) in anhydrous DMF (10 ml) was sequentially treated with DIPEA (1.1 ml), PyBOP, and 2M NH3 (3.6 ml). After 2 hours the product mixture was partitioned between 2M HCl(aq) and EtOAc. The organic layer was separated, washed with sat. NaHCO3(aq) solution, brine, then dried (MgSO4) and concentrated giving an orange oil (ca. 2 g). The product was purified by Biotage™ chromatography eluting with 5%→40% EtOAc/cyclohexane mixtures. The appropriate fractions were combined and concentrated to give the amide 90% pure (790 mg, 78%). m/z. 392.3 [M+formic acid-H]−.

Workup

  1. customAfter 2 hours the product mixture was partitioned between 2M HCl(aq) and EtOAc
  2. customThe organic layer was separated
  3. washwashed with sat. NaHCO3(aq) solution, brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3d92d8594ccd4995806f2527d88e49a9
Source dataset
uspto-grants-2012_09
Patent number
US08268839B2

Reaction notes

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