Dichloromethane → 5-(3-(2-Morpholinoethoxy)phenylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde

HRID 383678Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[CH:9][C:10]([CH:11]=[O:12])=[C:4]2[N:3]=1.[O:13]1[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][O:21][C:22]2[CH:23]=[C:24]([CH:26]=[CH:27][CH:28]=2)[NH2:25])[CH2:15][CH2:14]1.ClCCl>O1CCOCC1>[O:13]1[CH2:14][CH2:15][N:16]([CH2:19][CH2:20][O:21][C:22]2[CH:23]=[C:24]([NH:25][C:2]3[CH:7]=[CH:6][N:5]4[N:8]=[CH:9][C:10]([CH:11]=[O:12])=[C:4]4[N:3]=3)[CH:26]=[CH:27][CH:28]=2)[CH2:17][CH2:18]1

Participants

Conditions

Temperature: 120 °C

Procedure

To 5-chloropyrazolo[1,5-a]pyrimidine-3-carbaldehyde (40 mg, 0.221 mmol) in dioxane was added 3-(2-morpholinoethoxy)aniline (147 mg, 0.663 mmol). The mixture was heated in microwave at 120° C. Dichloromethane was added, and washed with water. The organic layer was dried over Na2SO4 and concentrated under reduced pressure to yield 5-(3-(2-morpholinoethoxy)phenylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde. The solid was used in the next step without further purification. LCMS (M+1=368)

Workup

washwashed with water
dry with materialThe organic layer was dried over Na2SO4
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-1754ed9bf10b4cdbb88287a7f146a3c7
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367681B2

Reaction notes

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