N-(3,4-dimethoxyphenethyl)-4-(6-methoxy-4-(piperazin-1-yl)naphthalen-2-yl)pyrimidin-2-amine → HCID 178487400, compound

HRID 1921991Notes

Reaction equation

HRID 1921991 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:33]=[CH:34][C:35]=1[O:36][CH3:37])[CH2:6][CH2:7][NH:8][C:9]1[N:14]=[C:13]([C:15]2[CH:24]=[C:23]([N:25]3[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([O:31][CH3:32])[CH:21]=3)[CH:16]=2)[CH:12]=[CH:11][N:10]=1.[Br:38][C:39]1[C:47]2[C:42](=[N:43][CH:44]=[N:45][C:46]=2Cl)[NH:41][N:40]=1>>[Br:38][C:39]1[C:47]2[C:42](=[N:43][CH:44]=[N:45][C:46]=2[N:28]2[CH2:27][CH2:26][N:25]([C:23]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([O:31][CH3:32])[CH:21]=4)[CH:16]=[C:15]([C:13]4[CH:12]=[CH:11][N:10]=[C:9]([NH:8][CH2:7][CH2:6][C:5]5[CH:33]=[CH:34][C:35]([O:36][CH3:37])=[C:3]([O:2][CH3:1])[CH:4]=5)[N:14]=4)[CH:24]=3)[CH2:30][CH2:29]2)[NH:41][N:40]=1

Participants

3

Reactant 2

HCID 67305590N-(3,4-dimethoxyphenethyl)-4-(6-methoxy-4-(piperazin-1-yl)naphthalen-2-yl)pyrimidin-2-amineHCID 1784783943-Bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine

Product 1

HCID 178487400HCID 178487400, compound

Procedure

4-{4-[4-(3-bromo-1H-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-6-methoxy-2-naphthyl}-N-[2-(3,4-dimethoxyphenyl)ethyl]pyrimidin-2-amine was synthesized according to General Procedure E except N-(3,4-dimethoxyphenethyl)-4-(6-methoxy-4-(piperazin-1-yl)naphthalen-2-yl)pyrimidin-2-amine and 3-bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine were used. 4-{4-[4-(3-bromo-1H-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-6-methoxy-2-naphthyl}-N-[2-(3,4-dimethoxyphenyl)ethyl]pyrimidin-2-amine 179 was isolated as a yellow solid. M.p.=130-133° C. 400 MHz 1H NMR (DMSO-d6) δ: 13.07 (br s, 1H), 8.39 (m, 3H), 7.98 (m, 2H), 7.73 (s, 1H), 7.27 (s, 1H), 6.91 (s, 1H), 6.85 (s, 2H), 6.44 (m, 1H), 4.02 (s, 3H), 3.80-3.76 (m, 8H), 3.41-3.39 (m, 4H), 2.95 (m, 2H), 2.84 (m, 2H); Experimental Elemental Analysis (1.73 equivalents of water and 0.38 equivalent of diethyl ether)=56.44% C, 4.74% H, 16.68% N; Calculated Elemental Analysis 56.44% C, 5.50% H, 16.68% N; LCMS (m/z): 697 [M+H].

Workup

  1. custom4-{4-[4-(3-bromo-1H-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-6-methoxy-2-naphthyl}-N-[2-(3,4-dimethoxyphenyl)ethyl]pyrimidin-2-amine was synthesized

Sources & evidence

ORD record
ord-859db4a5452c43a5aa0845d58d9ac4c1
Source dataset
uspto-grants-2012_05
Patent number
US08173808B2

Reaction notes

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