4-Ethyl-6-(4-fluorophenyl)pyrido[3,2-d]pyrimidin-2-amine → 2-Chloro-4-(2-[1,3]dioxan-2-yl-ethyl)-6-(4-fluorophenyl)-pyrido[3,2-d]pyrimidine

HRID 2196120Notes

Reaction equation

HRID 2196120 reaction equation
C(C1C2N=C(C3C=CC(F)=CC=3)C=CC=2N=C(N)N=1)C.[O:21]1[CH2:26][CH2:25][CH2:24][O:23][CH:22]1[CH2:27][CH2:28][Mg]Br.[Cl:31][C:32]1[N:33]=[C:34](Cl)[C:35]2[N:41]=[C:40]([C:42]3[CH:47]=[CH:46][C:45]([F:48])=[CH:44][CH:43]=3)[CH:39]=[CH:38][C:36]=2[N:37]=1>>[Cl:31][C:32]1[N:33]=[C:34]([CH2:28][CH2:27][CH:22]2[O:23][CH2:24][CH2:25][CH2:26][O:21]2)[C:35]2[N:41]=[C:40]([C:42]3[CH:47]=[CH:46][C:45]([F:48])=[CH:44][CH:43]=3)[CH:39]=[CH:38][C:36]=2[N:37]=1

Participants

4

Reactant 3

HCID 249638764-Ethyl-6-(4-fluorophenyl)pyrido[3,2-d]pyrimidin-2-amineHCID 596478432,4-Dichloro-6-(4-fluorophenyl)pyrido[3,2-d]pyrimidineHCID 178419673HCID 178419673, compound

Product 1

HCID 579067552-Chloro-4-(2-[1,3]dioxan-2-yl-ethyl)-6-(4-fluorophenyl)-pyrido[3,2-d]pyrimidine

Procedure

The procedure for the synthesis of 4-ethyl-6-(4-fluoro-phenyl)-pyrido[3,2-d]pyrimidin-2-ylamine was repeated, except for the use of (1,3-dioxan-2-ylethyl)magnesium bromide instead of ethylmagnesium bromide and 2,4-Dichloro-6-(4-fluoro-phenyl)-pyrido[3,2-d]pyrimidine (see WO2006135993) instead of N-[4-chloro-6-(4-fluoro-phenyl)-pyrido[3,2-d]pyrimidin-2-yl]-acetamide. The resulting title compound was characterised as follows: MS (m/z) 374.0 [M+H]+; HPLC Rt=4.46 minutes (Method A).

Sources & evidence

ORD record
ord-7077e9c1e5804b469fb20881dac3c192
Source dataset
uspto-grants-2012_12
Patent number
US08338435B2

Reaction notes

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