Trifluoroacetic acid water → ethyl 1-methyl-4-(3-(6-phenylpyridin-3-yl)-8H-pyrazolo[1,5-a]pyrrolo[3,2-e]pyrimidin-5-yl)cyclohex-3-enecarboxylate

HRID 1913272Notes

Reaction equation

HRID 1913272 reaction equation
C[Si](C)(C)CCOC[N:7](COCC[Si](C)(C)C)[C:8]1[N:13]2[N:14]=[CH:15][C:16]([C:17]3[CH:18]=[N:19][C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:21][CH:22]=3)=[C:12]2[N:11]=[C:10]([C:29]2[CH2:34][CH2:33][C:32]([CH3:40])([C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH2:31][CH:30]=2)[C:9]=1/[CH:41]=[CH:42]\OCC.C(O)(C(F)(F)F)=O.O>>[CH3:40][C:32]1([C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH2:33][CH2:34][C:29]([C:10]2[C:9]3[CH:41]=[CH:42][NH:7][C:8]=3[N:13]3[N:14]=[CH:15][C:16]([C:17]4[CH:18]=[N:19][C:20]([C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=5)=[CH:21][CH:22]=4)=[C:12]3[N:11]=2)=[CH:30][CH2:31]1

Participants

3

Reactant 2

HCID 22392675Trifluoroacetic acid waterHCID 68111075(Z)-ethyl 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-6-(2-ethoxyvinyl)-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-1-methylcyclohex-3-enecarboxylate

Product 1

HCID 136332421ethyl 1-methyl-4-(3-(6-phenylpyridin-3-yl)-8H-pyrazolo[1,5-a]pyrrolo[3,2-e]pyrimidin-5-yl)cyclohex-3-enecarboxylate

Procedure

(Z)-Ethyl 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-6-(2-ethoxyvinyl)-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-1-methylcyclohex-3-enecarboxylate (crude Int-18h) was treated with a mixture of 50% TFA/H2O at rt overnight. The reaction mixture was evaporated to dryness and purified by Prep-LC to give ethyl 1-methyl-4-(3-(6-phenylpyridin-3-yl)-8H-pyrazolo[1,5-a]pyrrolo[3,2-e]pyrimidin-5-yl)cyclohex-3-enecarboxylate (Int-18i). HPLC-MS tR=1.86 min (UV254nm); mass calculated for formula C29H27N5O2 477.2, observed LCMS m/z 478.3 (M+H).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. custompurified by Prep-LC

Sources & evidence

ORD record
ord-d5fecc8b95284f3b9113ae2eff300312
Source dataset
uspto-grants-2013_12
Patent number
US08609675B2

Reaction notes

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