tert-Butanol → N-(4-((3-(2-Amino-4-pyrimidinyl)-2-pyridinyl)oxy)phenyl)-4-(4-methyl-2-thienyl)-1-phthalazinamine

HRID 1408504Notes

Reaction equation

[NH2:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C:7]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([NH2:19])[N:14]=3)=[CH:11][CH:10]=[CH:9][N:8]=2)=[CH:4][CH:3]=1.Cl[C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26]([C:33]2[S:34][CH:35]=[C:36]([CH3:38])[CH:37]=2)=[N:25][N:24]=1.CC(O)(C)C>C(OCC)C.C(=O)([O-])[O-].[Na+].[Na+]>[NH2:19][C:15]1[N:14]=[C:13]([C:12]2[C:7]([O:6][C:5]3[CH:20]=[CH:21][C:2]([NH:1][C:23]4[C:32]5[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=5)[C:26]([C:33]5[S:34][CH:35]=[C:36]([CH3:38])[CH:37]=5)=[N:25][N:24]=4)=[CH:3][CH:4]=3)=[N:8][CH:9]=[CH:10][CH:11]=2)[CH:18]=[CH:17][N:16]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To 4-(2-(4-aminophenoxy)pyridin-3-yl)pyrimidin-2-amine and 1-chloro-4-(4-methyl-2-thienyl)phthalazine was added tBuOH. The resulting mixture was heated at 100° C. in a sealed tube for 16 hours. The reaction was diluted with diethyl ether and saturated sodium carbonate and vigorously shaken. The resulting solids were filtered and washed with water, diethyl ether and air dried to yield N-(4-((3-(2-amino-4-pyrimidinyl)-2-pyridinyl)oxy)phenyl)-4-(4-methyl-2-thienyl)-1-phthalazinamine as an off-white solid. MS m/z=504 [M+H]+. Calc'd for C28H21N7OS: 503.58.

Workup

filtrationThe resulting solids were filtered
washwashed with water, diethyl ether and air
customdried

Sources & evidence

ORD record: ord-fbbe2d21b6c549e798fa5b473ce09ab8
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921367B2

Reaction notes

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