Chloroacetaldehyde → 7-benzyl-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine

HRID 386620Notes

Reaction equation

[NH2:1][CH:2]1[NH:7][C:6](=O)[CH:5]=[C:4]([NH2:9])[NH:3]1.Cl[CH2:11][CH:12]=O.P(Cl)(Cl)([Cl:16])=O.[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[CH2:19]([N:9]1[C:4]2[N:3]=[C:2]([NH2:1])[N:7]=[C:6]([Cl:16])[C:5]=2[CH:12]=[CH:11]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

Reactant 4

HCID 33Chloroacetaldehyde

HCID 7498Benzyl Bromide

HCID 24813Phosphorus oxychloride

HCID 199675672,4-Diamino-6-oxodihydropyrimidine

Product 1

HCID 105873407-benzyl-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine

Procedure

In some embodiments, condensation of 2,6-diamino-1,2-dihydro[3H]pyrimidin-4-one with chloroacetaldehyde, followed by treatment with phosphorus oxychloride and anime protection with benzyl bromide provides 7-benzyl-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine. In some embodiments, this is coupled with optionally substituted (R1, R2, R3, R4) para-bromo phenol or thiol (T=O, S) or para-bromoaniline (T=NH). In some embodiments, conversion of amine to fluoro is achieved by treatment with HF-pyridine, and then coupled with para-V-aniline. In some embodiments, benzyl deprotection is achieved by treatment with aluminum chloride to give the desired compound.

Sources & evidence

ORD record: ord-067ea87fcd8a4978adfd23af028b0ae6
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372852B2

Reaction notes

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