methyl 2-chloro-4-morpholino-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate → Methyl 2-(2-fluoro-4-(3-(2-fluoroethyl)ureido)phenyl)-4-morpholino-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate

HRID 1626695Notes

Reaction equation

HRID 1626695 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]([NH:11][CH2:12][CH2:13][F:14])=[O:10])[CH:5]=[CH:4][C:3]=1[C:15]1[N:16]=[C:17]([N:29]2[CH2:34][CH2:33][O:32][CH2:31][C@@H:30]2C)[C:18]2[CH2:23][N:22]([C:24]([O:26][CH2:27]C)=[O:25])[CH2:21][C:19]=2[N:20]=1.ClC1N=C(N2CCOCC2)C2CN(C(OC)=O)CC=2N=1>>[F:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]([NH:11][CH2:12][CH2:13][F:14])=[O:10])[CH:5]=[CH:4][C:3]=1[C:15]1[N:16]=[C:17]([N:29]2[CH2:30][CH2:31][O:32][CH2:33][CH2:34]2)[C:18]2[CH2:23][N:22]([C:24]([O:26][CH3:27])=[O:25])[CH2:21][C:19]=2[N:20]=1

Participants

3

Reactant 2

HCID 86663169methyl 2-chloro-4-morpholino-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate2×HCID 86663175(S)-ethyl 2-(2-fluoro-4-(3-(2-fluoroethyl)ureido)phenyl)-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate

Product 1

HCID 86663176Methyl 2-(2-fluoro-4-(3-(2-fluoroethyl)ureido)phenyl)-4-morpholino-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylateYield 16%

Procedure

Method as (S)-Ethyl 2-(2-fluoro-4-(3-(2-fluoroethyl)ureido)phenyl)-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate (Example 168) using methyl 2-chloro-4-morpholino-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate (intermediate 25). Residue was then purified by prep. HPLC at low pH to afford a colourless solid (16%).

Workup

  1. customResidue was then purified by prep

Sources & evidence

ORD record
ord-ded5110c952a41899b8a4a93517e4bf8
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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