Ammonium formate → HCID 53806399, compound

HRID 258312Notes

Reaction equation

HRID 258312 reaction equation
[CH:1]1[C:14]2[C:13]3([CH2:16][N:17]4[CH2:22][CH2:21][CH:20]([NH:23][C:24]5[N:29]=[C:28]([NH2:30])[C:27]([N+:31]([O-])=O)=[CH:26][N:25]=5)[CH2:19][CH2:18]4)[CH2:15][CH:6]([C:7]4[C:12]3=[CH:11][CH:10]=[CH:9][CH:8]=4)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C([O-])=O.[NH4+]>C(OCC)(=O)C.CO.[Pd]>[CH:11]1[C:12]2[C:13]3([CH2:16][N:17]4[CH2:22][CH2:21][CH:20]([NH:23][C:24]5[N:29]=[C:28]([NH2:30])[C:27]([NH2:31])=[CH:26][N:25]=5)[CH2:19][CH2:18]4)[CH2:15][CH:6]([C:5]4[C:14]3=[CH:1][CH:2]=[CH:3][CH:4]=4)[C:7]=2[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 53690835HCID 53690835, compound

Product 1

HCID 53806399HCID 53806399, compoundYield 69.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

2-[1-(9,10-Dihydro-9,10-methanoanthracen-9-ylmethyl)-4-piperidylamino]-4-amino-5-nitropyrimidine (1.000 g, 2.3 mmol, prepared as described in Example 97), 0.2 weight equivalents of 10% Pd/C, and ammonium formate (1.000 g, 15.9 mmol) were combined in 20 mL 50% ethyl acetate/methanol and stirred under a nitrogen atmosphere at room temperature for 28 hours. The reaction mixture was filtered through celite and concentrated on a rotary evaporator to give the title compound as a tan glassy solid (0.643 g, 1.6 mmol, 69%), mp 138°-140° C.; MS(CI): 413 (M+H); NMR (250 MHz, DMSO-d6): 7.29-7.18(m, 5H), 6.98-6.87(m, 4H), 6.33(s, 2H), 5.75-5.72(br m, 1H), 4.32(s, 1H), 3.56(br m, 1H), 3.36(br m, 2H), 2.99-2.94(d, J=11.3 Hz, 2H), 2.47(s, 2H), 2.32-2.23(m, 2H), 1.80-1.75(m, 2H), 1.41-1.37(m, 2H).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-f447d75b95a84221b7e543e5a113a4f0
Source dataset
uspto-grants-1993_11
Patent number
US05266570

Reaction notes

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