5-Amino-3-methylisoxazole → 4'-Cyclopropylmethyl-N2-(3-methyl-isoxazol-5-yl)-[4,5']bipyrimidinyl-2,2'-diamine

HRID 1397143Notes

Reaction equation

HRID 1397143 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([NH2:7])[O:4][N:3]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH:18]1([CH2:21][C:22]2[C:27]([C:28]3[CH:33]=[CH:32][N:31]=[C:30](S(C)=O)[N:29]=3)=[CH:26][N:25]=[C:24]([NH2:37])[N:23]=2)[CH2:20][CH2:19]1>C1COCC1>[CH:18]1([CH2:21][C:22]2[C:27]([C:28]3[CH:33]=[CH:32][N:31]=[C:30]([NH:7][C:5]4[O:4][N:3]=[C:2]([CH3:1])[CH:6]=4)[N:29]=3)=[CH:26][N:25]=[C:24]([NH2:37])[N:23]=2)[CH2:19][CH2:20]1

Participants

5

Reactant 3

HCID 845905-Amino-3-methylisoxazoleHCID 2733832Lithium HexamethyldisilazideHCID 679839214'-(Cyclopropylmethyl)-2-(methylsulfinyl)-4,5'-bipyrimidin-2'-amine

Product 1

HCID 679833904'-Cyclopropylmethyl-N2-(3-methyl-isoxazol-5-yl)-[4,5']bipyrimidinyl-2,2'-diamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-methyl-isoxazol-5-ylamine in THF was added LiHMDS at −78° C., then the solution was stirred for 15 minutes, and 4′-(cyclopropylmethyl)-2-(methylsulfinyl)-4,5′-bipyrimidin-2′-amine (5-2) in THF was added to the reaction mixture. The reaction was warmed to rt and stirred for 1 hour. The reaction mixture was quenched with saturated ammonium chloride, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and evaporated to give a crude product which was further purified by reverse-phase HPLC to give the desired product.

Workup

  1. stirringstirred for 1 hour
  2. customThe reaction mixture was quenched with saturated ammonium chloride
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated
  6. customto give a crude product which
  7. customwas further purified by reverse-phase HPLC

Sources & evidence

ORD record
ord-6c1249d6069947a9bd151a30c5cab663
Source dataset
uspto-grants-2014_12
Patent number
US08901147B2

Reaction notes

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