Ammonia → HCID 67283784, compound

HRID 2111667Notes

Reaction equation

HRID 2111667 reaction equation
[Br:1][C:2]1[C:3]([NH:19][C:20]2[CH:24]=[C:23]([CH3:25])[NH:22][N:21]=2)=[N:4][C:5]([NH:8][CH2:9][C:10]2[O:14][N:13]=[C:12]([C:15](OC)=[O:16])[CH:11]=2)=[N:6][CH:7]=1.[NH3:26]>>[Br:1][C:2]1[C:3]([NH:19][C:20]2[CH:24]=[C:23]([CH3:25])[NH:22][N:21]=2)=[N:4][C:5]([NH:8][CH2:9][C:10]2[O:14][N:13]=[C:12]([C:15](=[O:16])[NH2:26])[CH:11]=2)=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 67284827HCID 67284827, compound

Product 1

HCID 67283784HCID 67283784, compoundYield 76%

Procedure

5-Bromo-2-[3-(methoxycarbonyl)isoxazol-5-ylmethylamino]-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidine (Example 104; 50 mg, 0.11 mmol) was suspended in 7N methanolic ammonia (5 ml) and stirred at ambient temperature for 18 hours. The volatiles were removed by evaporation and the residue was triturated with DCM/diethyl ether (50:50) and the product collected by filtration to give the title compound (35 mg, 76%). NMR (DMSO): 2.18 (s, 3H), 4.57 (d, 2H), 6.28 (br s, 1H), 6.50 (s, 1H), 7.72 (s, 2H), 8.01 (s, 1H), 8.05 (s, 1H), 12.06 (s, 1H); m/z 393 (MH)+.

Workup

  1. customThe volatiles were removed by evaporation
  2. customthe residue was triturated with DCM/diethyl ether (50:50)
  3. filtrationthe product collected by filtration

Sources & evidence

ORD record
ord-c41218d6c66e460381f8222428ca9486
Source dataset
uspto-grants-2009_04
Patent number
US07521453B2

Reaction notes

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