Dimethyl malonate → dimethyl 2-((4-chlorothiazol-2-yl)(5-(3-fluorophenyl)-1,3-dimethyl-2,4-dioxo-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-7-yl)methyl)malonate

HRID 2201264Notes

Reaction equation

HRID 2201264 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[Cl:11][C:12]1[N:13]=[C:14]([CH:17](O)[C:18]2[NH:19][C:20]([C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[CH:32]=3)=[C:21]3[C:26](=[O:27])[N:25]([CH3:28])[C:24](=[O:29])[N:23]([CH3:30])[C:22]=23)[S:15][CH:16]=1.[C:39]([O:46][CH3:47])(=[O:45])[CH2:40][C:41]([O:43][CH3:44])=[O:42]>C1COCC1>[Cl:11][C:12]1[N:13]=[C:14]([CH:17]([C:18]2[NH:19][C:20]([C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[CH:32]=3)=[C:21]3[C:26](=[O:27])[N:25]([CH3:28])[C:24](=[O:29])[N:23]([CH3:30])[C:22]=23)[CH:40]([C:39]([O:46][CH3:47])=[O:45])[C:41]([O:43][CH3:44])=[O:42])[S:15][CH:16]=1

Participants

5

Reactant 3

HCID 7943Dimethyl malonateHCID 2724254Sodium bis(trimethylsilyl)amideHCID 867234957-((4-Chlorothiazol-2-yl)(hydroxy)methyl)-5-(3-fluorophenyl)-1,3-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

Product 1

HCID 86723505dimethyl 2-((4-chlorothiazol-2-yl)(5-(3-fluorophenyl)-1,3-dimethyl-2,4-dioxo-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-7-yl)methyl)malonate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

NaHMDS solution (1M in THF, 7.13 mL, 7.13 mmol) was added slowly to a mixture of 7-((4-chlorothiazol-2-yl) (hydroxy)methyl)-5-(3-fluorophenyl)-1,3-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (Example 27, step 1) (1 g, 2.376 mmol), dimethyl malonate (0.819 mL, 7.13 mmol) and boron trifluoride THF complex (0.236 mL, 2.139 mmol) in THF (30 mL).

Sources & evidence

ORD record
ord-d61e9b43ea894300aad16e29509d784f
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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