2-Bromoaniline → HCID 22125151, compound

HRID 1858285Notes

Reaction equation

[CH:1]([C:3]1[C:4]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][O:19][CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][O:21]3)=[CH:14][CH:13]=2)=[N:5][C:6]([S:9][CH3:10])=[N:7][CH:8]=1)=O.[Br:26][C:27]1[CH:33]=[CH:32][CH:31]=[CH:30][C:28]=1[NH2:29]>>[Br:26][C:27]1[CH:33]=[CH:32][CH:31]=[CH:30][C:28]=1[NH:29][CH2:1][C:3]1[C:4]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][O:19][CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][O:21]3)=[CH:14][CH:13]=2)=[N:5][C:6]([S:9][CH3:10])=[N:7][CH:8]=1

Participants

Reactant 2

HCID 119922-Bromoaniline

HCID 22125053HCID 22125053, compound

Product 1

HCID 22125151HCID 22125151, compoundYield 24%

Procedure

Reaction of 4.0 g (11.1 mmol) of 5-formyl-4-[4-(tetrahydropyran-2-yloxymethyl)phenyl]amino-2-methylthiopyrimidine with 2-bromoaniline in a method analogous to Example 37(f) gave 1.13 g (24%) of 5-(2-bromoanilino)methyl-4-[4-(tetrahydropyran-2-yloxymethyl)phenyl]amino-2-methylthiopyrimidine as a pale yellow gum. [Mass spectrum (ESI) MH+ =515].

Sources & evidence

ORD record: ord-5e7005b7405343aab5696d533f17834e
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06150373

Reaction notes

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