Hydrochloric Acid → 3-(2-bromo-6-fluoro-phenyl)-7-(4,4-dioxo-3,4-dihydro-2H-4lambda*6*-benzo[1,4]oxathiin-6-ylamino)-1-methyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one

HRID 9730Notes

Reaction equation

HRID 9730 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[CH2:18][C:17]2[C:12](=[N:13][C:14](S(C)(=O)=O)=[N:15][CH:16]=2)[N:11]([CH3:23])[C:10]1=[O:24].[NH2:25][C:26]1[CH:27]=[CH:28][C:29]2[O:34][CH2:33][CH2:32][S:31](=[O:36])(=[O:35])[C:30]=2[CH:37]=1.Cl>CN1C(=O)CCC1.CCOCC>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[CH2:18][C:17]2[C:12](=[N:13][C:14]([NH:25][C:26]3[CH:27]=[CH:28][C:29]4[O:34][CH2:33][CH2:32][S:31](=[O:36])(=[O:35])[C:30]=4[CH:37]=3)=[N:15][CH:16]=2)[N:11]([CH3:23])[C:10]1=[O:24]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 219881503-(2-Bromo-6-fluorophenyl)-3,4-dihydro-7-methanesulphonyl-1-methylpyrimido[4,5-d]pyrimidin-2(1h)-oneHCID 219881516-Amino-2,3-dihydro-1,42×

Product 1

HCID 104147453-(2-bromo-6-fluoro-phenyl)-7-(4,4-dioxo-3,4-dihydro-2H-4lambda*6*-benzo[1,4]oxathiin-6-ylamino)-1-methyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

83 mg 3-(2-bromo-6-fluorophenyl)-3,4-dihydro-7-methanesulphonyl-1-methyl-pyrimido[4,5-d]pyrimidin-2(1H)-one and 80 mg 6-Amino-2,3-dihydro-benzo[1,4]oxathiine-4,4-dioxide (starting material h)) in 0.8 ml NMP were treated with 0.2 ml 2M HCl in ether and heated to 120° C. for 6 hrs. From this mixture 21 mg of the title product were isolated by preparative HPLC-MS (mp: 230–233° C.).

Sources & evidence

ORD record
ord-93ea8c40085e468c80b7e223c1b1aa11
Source dataset
uspto-grants-2006_08
Patent number
US07091345B2

Reaction notes

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