Dimethylformamide dimethyl acetal → HCID 178484322, compound

HRID 2091889Notes

Reaction equation

[Cl:1][C:2]1[N:3]=[C:4]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[C:5]2[N:11]=[C:10]([C:12]([NH2:14])=[O:13])[CH:9]=[CH:8][C:6]=2[N:7]=1.CO[CH:23](OC)[N:24]([CH3:26])[CH3:25]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[N:3]=[C:4]([N:15]2[CH2:16][CH2:17][O:18][CH2:19][CH2:20]2)[C:5]2[N:11]=[C:10]([C:12](/[N:14]=[CH:23]/[N:24]([CH3:26])[CH3:25])=[O:13])[CH:9]=[CH:8][C:6]=2[N:7]=1

Participants

Conditions

Temperature: 95 °C

Procedure

2-Chloro-4-morpholinopyrido[3,2-d]pyrimidine-6-carboxamide (90 mg) was suspended in toluene (5 mL) and treated with 1,1-dimethoxy-N,N-dimethylmethanamine (11 eq). The reaction was heated at 95° C. overnight then concentrated to dryness to afford crude (E)-2-chloro-N-((dimethylamino)methylene)-4-morpholinopyrido[3,2-d]pyrimidine-6-carboxamide. This intermediate was subsequently brought up in acetic acid (1.4 mL), isopropyl hydrazine hydrochloride was added and the reaction was stirred at room temperature for 1 hour. The reaction was concentrated to dryness then extracted with DCM and a saturated bicarbonate solution. The organic layer was dried (Mg2SO4), filtered and concentrated to give 0.11 g crude 4-(2-chloro-6-(1-isopropyl-1H-1,2,4-triazol-5-yl)pyrido[3,2-d]pyrimidin-4-yl)morpholine.

Workup

concentrationthen concentrated to dryness

Sources & evidence

ORD record: ord-4a9627a9e2df455891cc1f4b8484240a
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08440651B2

Reaction notes

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