Diisopropylethylamine → 5,6,7,8-tetrahydro-N-(4-(trifluoromethylsulfonyl)phenyl)pyrido[4,3-d]pyrimidin-4-amine

HRID 535356Notes

Reaction equation

HRID 535356 reaction equation
C([N:8]1[CH2:31][CH2:30][C:11]2[N:12]=[CH:13][N:14]=[C:15]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([S:23]([C:26]([F:29])([F:28])[F:27])(=[O:25])=[O:24])=[CH:19][CH:18]=3)[C:10]=2[CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)=O)C.C(N(CC)C(C)C)(C)C>C(Cl)(Cl)Cl>[F:29][C:26]([F:27])([F:28])[S:23]([C:20]1[CH:21]=[CH:22][C:17]([NH:16][C:15]2[C:10]3[CH2:9][NH:8][CH2:31][CH2:30][C:11]=3[N:12]=[CH:13][N:14]=2)=[CH:18][CH:19]=1)(=[O:24])=[O:25]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5213051-Chloroethyl chloroformateHCID 593465576-Benzyl-5,6,7,8-tetrahydro-N-(4-(trifluoromethylsulfonyl)phenyl)pyrido[4,3-d]pyrimidin-4-amine

Product 1

HCID 593464545,6,7,8-tetrahydro-N-(4-(trifluoromethylsulfonyl)phenyl)pyrido[4,3-d]pyrimidin-4-amineYield 83%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

6-Benzyl-5,6,7,8-tetrahydro-N-(4-(trifluoromethylsulfonyl)phenyl)pyrido[4,3-d]pyrimidin-4-amine (270 mg, 0.55 mmol) was dissolved in anhydrous chloroform (10 mL) and 1-chloroethylchloroformate was added (0.18 mL, 1.65 mmol). After stirring for 30 min, N,N-diisopropylethylamine was added (0.24 mL, 1.65 mmol) and the mixture was stirred for an additional 2 h. The chloroform was removed under vacuum and 30 ml of methanol was added and the mixture was heated for 30 min. Upon reaction completion, the methanol was removed and the residue was dissolved in ethyl acetate and washed with sat. NaHCO3 and brine. The organic layer was dried over Na2SO4, filtered and evaporated to give the product (163 mg, 83%).

Workup

  1. stirringthe mixture was stirred for an additional 2 h
  2. customThe chloroform was removed under vacuum and 30 ml of methanol
  3. additionwas added
  4. temperaturethe mixture was heated for 30 min
  5. customUpon reaction completion
  6. customthe methanol was removed
  7. dissolutionthe residue was dissolved in ethyl acetate
  8. washwashed with sat. NaHCO3 and brine
  9. dry with materialThe organic layer was dried over Na2SO4
  10. filtrationfiltered
  11. customevaporated

Sources & evidence

ORD record
ord-1edf54c3ae2a46ee9d95eba592fdb050
Source dataset
uspto-grants-2014_10
Patent number
US08859545B2

Reaction notes

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