Diisopropylethylamine → N-(4-(Trifluoromethyl)phenyl)-5,6,7,8-tetrahydro-2-(methoxymethyl)pyrido[3,4-d]pyrimidin-4-amine

HRID 2219964Notes

Reaction equation

ClC(OC(Cl)C)=O.C([N:15]1[CH2:24][CH2:23][C:22]2[C:21]([NH:25][C:26]3[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=3)=[N:20][C:19]([CH2:36][O:37][CH3:38])=[N:18][C:17]=2[CH2:16]1)C1C=CC=CC=1.C(N(C(C)C)CC)(C)C>ClCCCl>[F:35][C:32]([F:33])([F:34])[C:29]1[CH:30]=[CH:31][C:26]([NH:25][C:21]2[C:22]3[CH2:23][CH2:24][NH:15][CH2:16][C:17]=3[N:18]=[C:19]([CH2:36][O:37][CH3:38])[N:20]=2)=[CH:27][CH:28]=1

Participants

Conditions

Temperature: 60 °C

Procedure

1-Chloroethyl chloroformate (543 mg, 3.8 mmol) was added dropwise to the solution of 7-benzyl-N-(4-(trifluoromethyl)phenyl)-5,6,7,8-tetrahydro-2-(methoxymethyl)pyrido[3,4-d]pyrimidin-4-amine from Example 31 (820 mg, 1.9 mmol) and diisopropylethyl amine (490 mg, 3.8 mmol) in 1,2-dichloroethane (5 mL, anhydrous) at room temperature. After addition, the reaction mixture was stirred at 60° C. for 2 h in the atmosphere of nitrogen. Solvent was removed in vacuo, residue was dissolved in methanol (10 mL) and was stirred at 60° C. for 1 hr. Solvent was removed in vacuo, residue was dissolved in ethyl acetate and was washed by sodium bicarbonate aqueous solution, brine and dried over sodium sulfate. Solvent was removed in vacuo and light orange oily residue was directly taken to the next step.

Workup

additionAfter addition
customSolvent was removed in vacuo, residue
dissolutionwas dissolved in methanol (10 mL)
stirringwas stirred at 60° C. for 1 hr
customSolvent was removed in vacuo, residue
dissolutionwas dissolved in ethyl acetate
washwas washed by sodium bicarbonate aqueous solution, brine
dry with materialdried over sodium sulfate
customSolvent was removed in vacuo and light orange oily residue

Sources & evidence

ORD record: ord-f6e30175f127424789164b1090022f93
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07414131B2

Reaction notes

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