Diisopropylethylamine → 5-Bromo-2-(3-methylisoxazol-5-ylmethylamino)-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidine

HRID 2111665

Reaction equation

HRID 2111665 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[O:8][N:7]=[C:6]([CH3:9])[CH:5]=1.[Br:10][C:11]1[C:12]([NH:18][C:19]2[CH:23]=[C:22]([CH3:24])[NH:21][N:20]=2)=[N:13][C:14](Cl)=[N:15][CH:16]=1.C(N(CC)C(C)C)(C)C>C(O)CCC>[Br:10][C:11]1[C:12]([NH:18][C:19]2[CH:23]=[C:22]([CH3:24])[NH:21][N:20]=2)=[N:13][C:14]([NH:2][CH2:3][C:4]2[O:8][N:7]=[C:6]([CH3:9])[CH:5]=2)=[N:15][CH:16]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 45792534(3-Methyl-1,2-oxazol-5-yl)methanamine hydrochlorideHCID 509936455-bromo-2-chloro-N-(5-methyl-1H-pyrazol-3-yl)-4-Pyrimidinamine

Product 1

HCID 601542855-Bromo-2-(3-methylisoxazol-5-ylmethylamino)-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidineYield 31%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 5-aminomethyl-3-methylisoxazole hydrochloride (890 mg, 6.0 mmol), 5-bromo-2-chloro-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidine (Method 1; 578 mg, 2.0 mmol) and N,N-diisopropylethylamine (1.4 ml, 8.0 mmol) in 1-butanol (10 ml) was heated at 120° C. for 18 hours. The mixture was allowed to cool to ambient temperature and volatiles removed by evaporation. The residue was triturated with ether and the product collected by filtration to give the titled compound (225 mg, 31%). 1H NMR (DMSO): δ 2.15 (s, 3H), 2.2 (s, 3H), 4.5 (m, 2H), 6.1 (br s, 2H), 7.6 (br s, 1H), 8.0 (br s, 2H), 12.05 (br s, 1H); MS: m/z 366.

Workup

  1. temperatureto cool to ambient temperature
  2. customvolatiles removed by evaporation
  3. customThe residue was triturated with ether
  4. filtrationthe product collected by filtration

Sources & evidence

ORD record
ord-cf5dbee485fe4d8dbb0df7bc2ba3b85d
Source dataset
uspto-grants-2009_04
Patent number
US07521453B2

Linked notes

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