HCID 59507518, compound → HCID 23630334, compound

HRID 1512150Notes

Reaction equation

HRID 1512150 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[N:5]=[C:4]([O:14][CH:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]2)[CH:3]=1.NC1N=CC([C:35]2[N:40]=[C:39]([N:41]3CCOCC3)[N:38]=[C:37]([NH:47]C3C=NC4C(C=3)=C(OC)C=CC=4)[CH:36]=2)=CN=1>>[NH2:41][C:39]1[N:38]=[C:37]([NH2:47])[C:36]([C:2]2[N:7]=[C:6]([N:8]3[CH2:13][CH2:12][O:11][CH2:10][CH2:9]3)[N:5]=[C:4]([O:14][CH:15]3[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]3)[CH:3]=2)=[CH:35][N:40]=1.[O:11]1[CH2:10][CH2:9][N:8]([C:6]2[N:7]=[C:2]([C:36]3[C:37]([NH2:47])=[N:38][C:39]([NH2:41])=[N:40][CH:35]=3)[CH:3]=[C:4]([O:14][CH:15]3[CH2:16][CH2:17][NH:18][CH2:19][CH2:20]3)[N:5]=2)[CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 59507518HCID 59507518, compoundHCID 59507926HCID 59507926, compound

Product 2

HCID 23630334HCID 23630334, compoundHCID 59508005HCID 59508005, compound

Procedure

tert-butyl 4-(6-(2,4-diaminopyrimidin-5-yl)-2-morpholinopyrimidin-4-yloxy)piperidine-1-carboxylate was prepared by Suzuki reaction tert-butyl 4-(6-chloro-2-morpholinopyrimidin-4-yloxy)piperidine-1-carboxylate, as shown in Step 2 of Example 19, with 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine-2,4-diamine (prepared as in Method 7). The crude product was purified by reverse phase HPLC and isolated as the free base after extraction into EtOAc upon basifying (70%). LCMS (m/z): 473.1 (MH+). The title compound was prepared by cleaving the N-Boc protecting group as shown in Step 3 of Example 19. LCMS (m/z): 373.0 (MH+).

Workup

  1. customThe crude product was purified by reverse phase HPLC
  2. customisolated as the free base
  3. extractionafter extraction into EtOAc

Sources & evidence

ORD record
ord-c9902244e7014b2eb0efbc6d340cf7b6
Source dataset
uspto-grants-2012_07
Patent number
US08217035B2

Reaction notes

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