Sodium bis(trimethylsilyl)amide → 5-(6-morpholinopyridin-3-ylamino)-7-chloropyrido[4,3-d]pyrimidin-4(3H)-one

HRID 1805754Notes

Reaction equation

HRID 1805754 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[N:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.NC1C=CC=CC=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Cl[C:32]1[C:41]2[C:40](=[O:42])[NH:39][CH:38]=[N:37][C:36]=2[CH:35]=[C:34]([Cl:43])[N:33]=1>C1COCC1>[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[N:12]=[CH:11][C:10]([NH:13][C:32]3[C:41]4[C:40](=[O:42])[NH:39][CH:38]=[N:37][C:36]=4[CH:35]=[C:34]([Cl:43])[N:33]=3)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 86649543Aniline 6-morpholinopyridin-3-amineHCID 1357415885,7-Dichloropyrido[4,3-d]pyrimidin-4(3H)-one

Product 1

HCID 1361111765-(6-morpholinopyridin-3-ylamino)-7-chloropyrido[4,3-d]pyrimidin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At 0° C., to a solution of aniline 6-morpholinopyridin-3-amine (II) (125 mg, 0.7 mmol) in THF (3 mL) was added NaHMDS (2 mL, 1M/THF). After 10 minutes, compound 5,7-dichloropyrido[4,3-d]pyrimidin-4(3H)-one (I) (108 mg, 0.5 mmol) was added. The resulting mixture was stirred for 4 hours. The mixture was subjected to HPLC-MS, and the product 5-(6-morpholinopyridin-3-ylamino)-7-chloropyrido[4,3-d]pyrimidin-4(3H)-one was obtained as a purple solid.

Sources & evidence

ORD record
ord-e7e36075cb7545eaa0f3e89fa45962cf
Source dataset
uspto-grants-2013_01
Patent number
US08354526B2

Reaction notes

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