Water → 3-{7-[2-(4-Methyl-piperazin-1-yl)-pyridin-4-yl]-2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl}-phenol

HRID 912099Notes

Reaction equation

C[O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:10]3[CH2:23][CH2:22][N:21]([C:24]4[CH:29]=[CH:28][N:27]=[C:26]([N:30]5[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32][CH2:31]5)[CH:25]=4)[C:11]=3[N:12]=[C:13]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[N:14]=2)[CH:6]=[CH:7][CH:8]=1.C([S-])C.[Na+].O>CN(C)C=O>[CH3:36][N:33]1[CH2:34][CH2:35][N:30]([C:26]2[CH:25]=[C:24]([N:21]3[C:11]4[N:12]=[C:13]([N:15]5[CH2:16][CH2:17][O:18][CH2:19][CH2:20]5)[N:14]=[C:9]([C:5]5[CH:4]=[C:3]([OH:2])[CH:8]=[CH:7][CH:6]=5)[C:10]=4[CH2:23][CH2:22]3)[CH:29]=[CH:28][N:27]=2)[CH2:31][CH2:32]1

Participants

Conditions

Temperature: 150 °C

Procedure

4-(3-Methoxyphenyl)-7-[2-(4-methylpiperazin-1-yl)-pyridin-4-yl]-2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine (107 mg, 0.22 mmol) was heated at 150° C. in dimethylformamide (1 ml), and sodium ethanethiolate (275 mg, 3.3 mmol) was added at 15 minutes intervals in 3 portions. After heating at 150° C. for further 15 minutes followed by cooling, water (1 ml) was added, followed by washing with ethyl acetate (2 ml). After the aqueous layer was left overnight, the deposited precipitate was filtered off, and washed with water followed by drying, whereby a colorless solid was obtained (18 mg, 17.3% yield).

Workup

temperatureby cooling
washby washing with ethyl acetate (2 ml)
filtrationthe deposited precipitate was filtered off
washwashed with water
customby drying
customwhereby a colorless solid was obtained (18 mg, 17.3% yield)

Sources & evidence

ORD record: ord-4fe883bd4a274716823750cd9e93f022
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022205B2

Reaction notes

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