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

HRID 971237Notes

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 a mixture 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 under 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 with saturated aqueous sodium bicarbonate, brine and dried over sodium sulfate. Solvent was removed in vacuo and light orange oily residue which was usd directly in 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 with saturated aqueous sodium bicarbonate, brine
dry with materialdried over sodium sulfate
customSolvent was removed in vacuo and light orange oily residue which

Sources & evidence

ORD record: ord-7f087ffef9824cf4b7d6eaab57c57f22
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07312330B2

Reaction notes

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