Phenothiazine → 9-[(2,4-Diaminofuro[2,3-d]pyrimidin-5-yl)methyl]phenothiazine

HRID 1827713Notes

Reaction equation

HRID 1827713 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([NH2:25])[C:5]2[C:10]([CH2:11]N(C3C=CC=CC=3)C3C=CC=CC=3)=[CH:9][O:8][C:6]=2[N:7]=1.[CH:26]1[C:39]2[NH:38][C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[S:31][C:30]=2[CH:29]=[CH:28][CH:27]=1.[H-].[Na+].NC1N=C(N)C2C(CCl)=COC=2N=1>>[NH2:1][C:2]1[N:3]=[C:4]([NH2:25])[C:5]2[C:10]([CH2:11][C:36]3[CH:35]=[CH:34][CH:33]=[C:32]4[C:37]=3[NH:38][C:39]3[CH:26]=[CH:27][CH:28]=[CH:29][C:30]=3[S:31]4)=[CH:9][O:8][C:6]=2[N:7]=1

Participants

5

Reactant 4

HCID 7108PhenothiazineHCID 24758Sodium hydrideHCID 9818937n-[(2,4-Diaminofuro[2,3-d]pyrimidin-5-yl)methyl]-n,n-diphenylamineHCID 114129595-(Chloromethyl)furo[2,3-d]pyrimidine-2,4-diamine

Product 1

HCID 220629809-[(2,4-Diaminofuro[2,3-d]pyrimidin-5-yl)methyl]phenothiazine

Procedure

9-[(2,4-Diaminofuro[2,3-d]pyrimidin-5-yl)methyl]phenothiazine (Formula I: Ar=2,4-diaminofuro[2,3-d]pyrimidin-5-yl; W=CH2; X=N; Z=S; m=n=0) is prepared similarly to N-[(2,4-diaminofuro[2,3-d]pyrimidin-5-yl)methyl]-N,N-diphenylamine as disclosed above by using phenothiazine (159 mg, 0.8 mmol), NaH (50 mg, 2.1 mmol), and 2,4-diamino-5-chloromethylfuro[2,3-d]pyrimidine (60 mg, 0.3 mmol). The product can be purified by chromatography.

Workup

  1. customThe product can be purified by chromatography

Sources & evidence

ORD record
ord-75a372aab9214ff0a3a9ac9ee10b4b18
Source dataset
uspto-grants-2006_06
Patent number
US07056911B1

Reaction notes

Loading…